4-(Chloromethyl)benzophenone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis of 9'-(4-benzoylbenzyl)-9H-adenine (20) was achieved by the following procedure (Scheme 9). A mixture of 6-chloropurine (3.09 g, 20 mmol), 4-benzoyl-benzyl chloride (6.05 g, 22 mmol) and K2CO3 (3.04 g, 22 mmol) in DMF (50 ml) was stirred overnight at rt, diluted with water (400 ml), and extracted with EtOAc (3×100 ml) (Scheme 9)52. The combined organic layers were washed with water and brine, dried over MgSO4, concentrated in vacuo, and subjected to flash-chromatography on silica gel eluting with CH2Cl2 -acetone (80:20). The fractions containing the higher Rf, the major component, were combined and concentrated in vacuo to give 2.86 g (41%) of 9-(4-benzoylbenzyl)-6-chloro-9H-purine. To a solution of this iminochloride (1.05 g, 3 mmol) in EtOH (20 ml) was added a 2M solution of NH3 in MeOH. This medium was warmed overnight at 90° C. under pressure (constant volume). It was then cooled and concentrated in vacuo. The residue was washed successively with a 1M solution of NaHCO3, water, iPrOH, and hot CH2Cl2, and then was recrystallized from butanol to give 0.53 g (54%) of 9-(4-benzoylbenzyl)-9H-adenine (20). 1H NMR (DMSO) δ 5.49 (s, 2H, CH2), 7.27-7.71 (m, 9H, H--Ar), 8.15 (s, 1H, H-2), 8.30 (s, 1H, H-8). ##STR10## Synthesis of 9-[(4-bis-phenyl)buten-4-yl]-9H-adenine (21) extracted with EtOAc (3×100 ml) (Scheme 9)52 The combined organic layers were washed with water and brine dried over MgSO4 concentrated in vacuo The fractions containing the higher Rf concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 150 g of formamide are stirred together with 90 mL of 30%ig sodium methylate solution for 8 hours under slight vacuum at 80° C. To the resulting solution of sodium diformylamide there are added 150 g of 4-chloromethylbenzophenone. After 15 hours the suspension originally present has changed to a clear solution which is added to 1l of 10%ig sodium carbonate solution. A solid material precipitates, which is filtered off in vacuo and dried. A solid material precipitates which is filtered off in vacuo dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 196.2 g of 4-methylbenzophenone are dissolved in chlorobenzene and then gassed at 80° C. in the presence of 1.6 g of AIBN (azodiisobutyronitrile) with a total of 71.0 g of chlorine. The reaction mixture is concentrated and the solid material obtained recrystallized from 1 L of ethanol. The reaction mixture is concentrated the solid material obtained recrystallized from 1 L of ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis of 9-(4-benzoylbenzyl) -9H-adenine (20) was achieved by the following procedure (Scheme 9). A mixture of 6-chloropurine (3.09 g, 20 mmol), 4-benzoyl-benzyl chloride (6.05 g, 22 mmol)and K2CO3 (3.04 g, 22 mmol) in DMF (50 ml) was stirred overnight at rt, diluted with water (400 ml), and extracted with EtOAc (3×100 ml) (Scheme 9)52. The combined organic layers were washed with water and brine, dried over MgSO4, concentrated in vacuo, and subjected to flash-chromatography on silica gel eluting with CH2Cl2 -acetone (80:20). The fractions containing the higher Rf, the major component, were combined and concentrated in vacuo to give 2.86 g (41%) of 9-(4-benzoylbenzyl)-6-chloro-9H-purine. To a solution of this iminochloride (1.05 g, 3 mmol) in EtOH (20 ml) was added a 2M solution of NH3 in MeOH. This medium was warmed overnight at 90° C. under pressure (constant volume). It was then cooled and concentrated in vacuo. The residue was washed successively with a 1M solution of NaHCO3, water, iPrOH, and hot CH2Cl2, and then was recrystallized from butanol to give 0.53 g (54%) of 9-(4-benzoylbenzyl)-9H-adenine (20). 1H NMR (DMSO) δ 5.49 (s, 2H, CH2), 7.27-7.71 (m, 9H, H-Ar), 8.15 (s, 1H, H-2), 8.30 (s, 1H, H-8). ##STR10## Synthesis of 9-[(4-bis-phenyl)buten-4-yl]-9H-adenine (21) extracted with EtOAc (3×100 ml) (Scheme 9)52 The combined organic layers were washed with water and brine dried over MgSO4 concentrated in vacuo The fractions containing the higher Rf concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis of 9'-(4-benzoylbenzyl)-9H-adenine (20) was achieved by the following procedure (Scheme 9). A mixture of 6-chloropurine (3.09 g, 20 mmol), 4-benzoyl-benzyl chloride (6.05 g, 22 mmol) and K2CO3 (3.04 g, 22 mmol) in DMF (50 ml) was stirred overnight at rt, diluted with water (400 ml), and extracted with EtOAc (3×100 ml) (Scheme 9)52. The combined organic layers were washed with water and brine, dried over MgSO4, concentrated in vacuo, and subjected to flash-chromatography on silica gel eluting with CH2Cl2 -acetone (80:20). The fractions containing the higher Rf, the major component, were combined and concentrated in vacuo to give 2.86 g (41%) of 9-(4-benzoylbenzyl)-6-chloro-9H-purine. To a solution of this iminochloride (1.05 g, 3 mmol) in EtOH (20 ml) was added a 2M solution of NH3 in MeOH. This medium was warmed overnight at 90° C. under pressure (constant volume). It was then cooled and concentrated in vacuo. The residue was washed successively with a 1M solution of NaHCO3, water, iPrOH, and hot CH2Cl2, and then was recrystallized from butanol to give 0.53 g (54%) of 9-(4-benzoylbenzyl)-9H-adenine (20). 1H NMR (DMSO) δ 5.49 (s, 2H, CH2), 7.27-7.71 (m, 9H, H--Ar), 8.15 (s, 1H, H-2), 8.30 (s, 1H, H-8). ##STR10## Synthesis of 9-[(4-bis-phenyl)buten-4-yl]-9H-adenine (21) extracted with EtOAc (3×100 ml) (Scheme 9)52 The combined organic layers were washed with water and brine dried over MgSO4 concentrated in vacuo The fractions containing the higher Rf concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 150 g of formamide are stirred together with 90 mL of 30%ig sodium methylate solution for 8 hours under slight vacuum at 80° C. To the resulting solution of sodium diformylamide there are added 150 g of 4-chloromethylbenzophenone. After 15 hours the suspension originally present has changed to a clear solution which is added to 1l of 10%ig sodium carbonate solution. A solid material precipitates, which is filtered off in vacuo and dried. A solid material precipitates which is filtered off in vacuo dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 150 g of formamide are stirred together with 90 mL of 30%ig sodium methylate solution for 8 hours under slight vacuum at 80° C. To the resulting solution of sodium diformylamide there are added 150 g of 4-chloromethylbenzophenone. After 15 hours the suspension originally present has changed to a clear solution which is added to 1l of 10%ig sodium carbonate solution. A solid material precipitates, which is filtered off in vacuo and dried. A solid material precipitates which is filtered off in vacuo dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 196.2 g of 4-methylbenzophenone are dissolved in chlorobenzene and then gassed at 80° C. in the presence of 1.6 g of AIBN (azodiisobutyronitrile) with a total of 71.0 g of chlorine. The reaction mixture is concentrated and the solid material obtained recrystallized from 1 L of ethanol. The reaction mixture is concentrated the solid material obtained recrystallized from 1 L of ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 25 milliliters of 2-methoxyethanol was added, with magnetic stirring, 5.0 grams (0.75 mole) of 85% potassium hydroxide pellets dissolved in 5 milliliters water. The amount of 5.0 grams (0.0216 mole) of 4-(chloromethyl)benzophenone was added, the mixture was refluxed for three hours, filtered with suction, and concentrated. Water was added and the oil which separated was isolated by extraction with ether to provide 5.0 grams (86% yield) of 4-(2-methoxyethoxymethyl)benzophenone as an orange colored liquid. Infrared analysis revealed the presence of a carbonyl band at 1660 cm-1. Ultraviolet analysis revealed λ max (ε) at 256 nanometers (18,380). the mixture was refluxed for three hours filtered with suction concentrated Water was added the oil which separated was isolated by extraction with ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1 liter of absolute ethyl alcohol was added 80 grams (1.2 moles) of 85% potassium hydroxide pellets with mechanical stirring. The amount of 115 grams (0.5 moles) of 4-(chloromethyl)benzophenone was added to the resulting warm solution. The reaction mixture was refluxed for three hours, filtered with suction, and concentrated. Water was added and the lower oily layer was separated and distilled to provide 102 grams (84% yield) of 4-(ethoxymethyl)benzophenone. Infrared analysis revealed the presence of a carbonyl band at 1660 cm-1. Ultraviolet analysis revealed λ max (ε) of 256 nanometers (18,360). Proton nuclear magnetic resonance analysis revealed the following where m is a multiplet, s is a singlet, q is a quartet, t is a triplet and TMS is tetramethylsilane. warm solution The reaction mixture was refluxed for three hours filtered with suction concentrated Water was added the lower oily layer was separated distilled