1-bromo-4-methylpentan-2-one

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottomed flask 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 6, 0.95 g, 3.13 mmol) and 1-bromo-4-methylpentan-2-one (0.561 g, 3.13 mmol, Chem. Pharm. Bull., 2001, 49(8), 988-998) were mixed in EtOH (10 mL) to give a yellow suspension. The reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. ACN was added, and the residue solid was azeotroped with ACN (3×). The crude mass obtained, 1.02 g, was taken forward without purification. to give a yellow suspension The reaction mixture was cooled to room temperature concentrated under reduced pressure ACN was added the residue solid was azeotroped with ACN (3×) The crude mass obtained 1.02 g, was taken forward without purification

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

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

Procedure: A solution of 676 mg a 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir), 18 mL N,N-dimethylformamide (DMF), and 200 mg sodium hydride (80%) was stirred at room temperature for 15 min, then 0.7 mL 4-methyl-1-bromopentan-2-one was added dropwise into the solution. Changing to dark-brown color, the solution was stirred at room temperature for 3 hr, added 15 mL ammonia, and was continuously stirred overnight. The solvent was removed to obtain a residue, which was purified by column chromatography (silica gel) with an elute of chloroform/methanol (6/1) to obtain an oil. Recrystallization of the oil produced compound 1. was continuously stirred overnight The solvent was removed to obtain a residue, which was purified by column chromatography (silica gel) with an elute of chloroform/methanol (6/1) to obtain an oil Recrystallization of the oil

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

Procedure: Bromomethylisobutyl ketone (53.6 g) and triphenylphosphine (78.5 g) are intimately mixed in a 500 ml round-bottom flask and, after the initially strong heat tonality subsides, are left for 12 hours under nitrogen at room temperature. After that, the solid reaction mass is taken up in 330 ml of methylene chloride and refluxed for 30 minutes. After adding 500 ml of ether, it is allowed to cool to room temperature and the product is isolated by filtration. After drying,111.7 g of the phosphonium salt with a melting point of 244-245° C. is obtained. After that, the solid reaction mass refluxed for 30 minutes the product is isolated by filtration After drying

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve 1-bromo-4-methyl-2-pentanone (11.0 g, 61.4 mmol) and potassium phthalimide (11.9 g, 64.5 mmol) in toluene (60 mL) at room temperature under a nitrogen atmosphere. Heat the mixture to 100° C. and stir for 16 h. Cool the resulting slurry to room temperature, filter off solids, and concentrate the filtrate in vacuo to a solid. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (1:1) to obtain the desired intermediate (3.6 g, 24%). MS (ES+) m/z: 246.3 (M+H)+. Cool the resulting slurry to room temperature filter off solids concentrate the filtrate in vacuo to a solid Purify the residue by chromatography on silica gel (40 g) eluting with hexane/EtOAc (1:1)

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

Procedure: 100 mg (about 0.182 mmol) of the compound from Example 115A and 49 mg (0.273 mmol) of 1-bromo-4-methylpentan-2-one (J. Org. Chem., 19, 2005, 4141-4153) were reacted according to the General Method 3. Yield: 50 mg (55% of theory).

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

Procedure: 150 mg (about 0.315 mmol) of the compound from Example 53A and 76 mg (0.426 mmol) of 1-bromo-4-methylpentan-2-one (J. Org. Chem., 19, 2005, 4141-4153) were reacted according to the General Method 3. Yield: 68 mg (40% of theory).

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

Procedure: 53.6 g of bromomethyl isobutyl ketone is added to 78.5 g of triphenylphosphine and the cooled reaction mixture is recrystallized in methylene chloride/ether (1:2). 111.7 g of isobutylcarbonylmethyltriphenylphosphonium bromide with a melting point of 244°-245° C., is obtained. the cooled reaction mixture is recrystallized in methylene chloride/ether (1:2)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 100 mL round-bottomed flask 5-bromo-2-(3-ethylureido)pyridine-4-carbothioamide (Intermediate 6, 0.95 g, 3.13 mmol) and 1-bromo-4-methylpentan-2-one (0.561 g, 3.13 mmol, Chem. Pharm. Bull., 2001, 49(8), 988-998) were mixed in EtOH (10 mL) to give a yellow suspension. The reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. ACN was added, and the residue solid was azeotroped with ACN (3×). The crude mass obtained, 1.02 g, was taken forward without purification. to give a yellow suspension The reaction mixture was cooled to room temperature concentrated under reduced pressure ACN was added the residue solid was azeotroped with ACN (3×) The crude mass obtained 1.02 g, was taken forward without purification