[2-(dimethylamino)phenyl]methanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture containing 0.71 g (5 mmol) of 6-methyl-2-thiouracil, 0.76 g (5 mmol) of 2-dimethylaminobenzyl alcohol (J. Chem. Soc. 1954, 4127) and 5 ml of concentrated hydrochloric acid is stirred at 60° C. for 3 hours, then cooled and made alkaline by adding 5N sodium hydroxide solution under cooling by ice. The mixture is extracted 3 times with 20 ml of chloroform each. After combining the organic phase is washed with sodium carbonate solution and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated. The residue is twice recrystallized from ethyl acetate to yield 0.59 g (43%) of the title compound, m.p.: 151°-153° C. cooled under cooling by ice The mixture is extracted 3 times with 20 ml of chloroform each is washed with sodium carbonate solution with saturated sodium chloride solution, dried over anhydrous magnesium sulfate evaporated The residue is twice recrystallized from ethyl acetate

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

Procedure: In a 250 mL round-bottomed flask, (3-(dimethylamino)phenyl)methanol (1 g) and paraformaldehyde (2.5 g) were added to acetic acid (150 mL) to give a suspension. Sodium cyanoborohydride (2.6 g) was added slowly. The mixture was stirred at room temperature overnight. After concentration of the solvent, water and ethyl acetate (1:1, 100 mL) were added. After separation, the aqueous layer was extracted by ethyl acetate (2×20 mL). The combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL), and dried over Na2SO4. After filtration and concentration, the residue was taken up into CH2Cl2 and the product was purified by flash chromatography (Varian, Superflash SF40-80 g column), eluting with 0-20% methanol/dichloromethane, to provide the title compound. to give a suspension After separation the aqueous layer was extracted by ethyl acetate (2×20 mL) The combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL) dried over Na2SO4 After filtration and concentration the product was purified by flash chromatography (Varian, Superflash SF40-80 g column) eluting with 0-20% methanol/dichloromethane

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

Procedure: In a 250 mL round-bottomed flask, (3-(dimethylamino)phenyl)methanol (1 g) and paraformaldehyde (2.5 g) were added to acetic acid (150 mL) to give a suspension. Sodium cyanoborohydride (2.6 g) was added slowly. The mixture was stirred at room temperature overnight. After concentration of the solvent, water and ethyl acetate (1:1, 100 mL) were added. After separation, the aqueous layer was extracted by ethyl acetate (2×20 mL). The combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL), and dried over Na2SO4. After filtration and concentration, the residue was taken up into CH2Cl2 and the product was purified by flash chromatography (Varian, Superflash SF40-80 g column), eluting with 0-20% methanol/dichloromethane, to provide the title compound. to give a suspension After separation the aqueous layer was extracted by ethyl acetate (2×20 mL) The combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL) dried over Na2SO4 After filtration and concentration the product was purified by flash chromatography (Varian, Superflash SF40-80 g column) eluting with 0-20% methanol/dichloromethane