methyl methanesulfonate

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

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

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

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

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

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

Procedure: Compound No. 46. A suspension of 4-phenylamino-2-amino-6-methylpyrimidine, Compound No. 45, (0.25 g) in ethanol (4 mL) was treated with methyl methanesulfonate (0.090 g) and heated at reflux for 5 days. Additional methyl methanesulfonate (0.090 g) was added and the mixture refluxed another 2 days. Concentration and recrystallization from a mixture of methanol, ethyl acetate, and tert-butyl ethyl ether gave 0.10 g of 4-phenylamino-2-amino-1,6-dimethylpyrimidinium methanesulfonate. heated at reflux for 5 days the mixture refluxed another 2 days Concentration and recrystallization from a mixture of methanol, ethyl acetate, and tert-butyl ethyl ether

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

Procedure: Compound No. 46. A suspension of 4-phenylamino-2-amino-6-methylpyrimidine, Compound No. 45, (0.25 g) in ethanol (4 mL) was treated with methyl methanesulfonate (0.090 g) and heated at reflux for 5 days. Additional methyl methanesulfonate (0.090 g) was added and the mixture refluxed another 2 days. Concentration and recrystallization from a mixture of methanol, ethyl acetate, and tert-butyl ethyl ether gave 0.10 g of 4-phenylamino-2-amino-1,6-dimethylpyrimidinium methanesulfonate. heated at reflux for 5 days the mixture refluxed another 2 days Concentration and recrystallization from a mixture of methanol, ethyl acetate, and tert-butyl ethyl ether

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

Procedure: A mixture of 2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (2.67 g, 14.2 mmol), methanesulfonic acid methyl ester (1.26 mL, 14.9 mmol) and cesium carbonate (9.25 g, 28.4 mmol) in anhydrous N,N-dimethylformamide (21 mL) was stirred at RT (room temperature) under N2 for 15 h. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with 1:1 water/brine (3×) and brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 2.50 g (87.1%) of 2,4-dichloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidine as a white solid. MS(ESI) m/z: 202.2/204.1 [M+1]+. the organic layer was washed with 1:1 water/brine (3×) and brine (1×) dried over Na2SO4 filtered concentrated in vacuo The crude product was purified by silica gel chromatography

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

Procedure: Twenty grams of 1-(2-hydroxyethyl)-2-imidazolinethione and methyl methanesulfonate (12.75 ml) are dissolved in ethyl alcohol (90 mL) and refluxed for 2 hours. The mixture is cooled to room temperature and diluted with t-butyl methyl ether (1 liter). An oil separates which solidifies on keeping the mixture in the freezer at -20° C. for a few days. The solid is then filtered, washed with butyl methyl ether and dried to give 1-(2-hydroxyethyl)-2-methylthioimidazoline mesylate, melting point 78.9°-81.5° C. refluxed for 2 hours at -20° C. for a few days The solid is then filtered washed with butyl methyl ether dried

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

Procedure: Then, 1-(2-hydroxyethyl)-3,4,5,6-tetrahydropyrimidine-2-thione (121.2 g) and methyl methanesulfonate (91.51 g) are heated at reflux in ethyl alcohol (200 ml) for about 2 hours and then allowed to cool to room temperature. The mixture was diluted with t-butyl methyl ether (2 liters). An oil separates which crystallizes on keeping in freezer at -20° C. Filtration and drying yields 145.7 g of 1-(2-hydroxyethyl)-2-methylthio-3,4,5,6-tetrahydropyrimidine mesylate, melting point 61.7°-62.2° C. An oil separates which crystallizes on keeping in freezer at -20° C Filtration drying

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

Procedure: Then, 1-(2-hydroxyethyl)-3,4,5,6-tetrahydropyrimidine-2-thione (121.2 g) and methyl methanesulfonate (91.51 g) are heated at reflux in ethyl alcohol (200 ml) for about 2 hours and then allowed to cool to room temperature. The mixture was diluted with t-butyl methyl ether (2 liters). An oil separates which crystallizes on keeping in freezer at -20° C. Filtration and drying yields 145.7 g of 1-(2-hydroxyethyl)-2-methylthio-3,4,5,6-tetrahydropyrimidine mesylate, melting point 61.7°-62.2° C. An oil separates which crystallizes on keeping in freezer at -20° C Filtration drying

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 10 ml of chloroform are dissolved 0.48 g of 2-[(2-methoxy-3-octadecyloxypropyl)sulfonyl]ethyldimethylamine and 1 g of methyl methanesulfonate and the solution is stirred at 70° C. for 5 hours. Then the reaction mixture is concentrated under reduced pressure and the residue is crystallized from chloroform and ether to give 417 mg of the captioned compound. Then the reaction mixture is concentrated under reduced pressure the residue is crystallized from chloroform and ether