反应详情

A mixture of 8.4 g (33 mmol) of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinecarboxylic acid and 0.50 mL (0.47 g, 6.5 mmol) of N,N-dimethylformamide in 120 mL of dichloromethane was cooled in ice and treated dropwise with a solution of 4.9 mL (7.1 g, 56 mmol) of oxalyl chloride in 18 mL of dichloromethane. The mixture was stirred with ice cooling for 2 hours, then filtered, and evaporated. The residual crude acid chloride was redissolved in 85 mL of dichloromethane and added dropwise to an ice-cooled mixture of 4.0 g (41 mmol) of N,O-dimethylhydroxylamine hydrochloride and 15 mL (12.2 g, 123 mmol) of 1-methylpiperidine in 150 mL of dichloromethane. The mixture was stirred at room temperature for 16 hours, then washed with 0.4N hydrochloric acid, brine, 5% aqueous sodium bicarbonate, and brine again. The organic layer was dried (anhydrous sodium sulfate) and evaporated, and the residue recrystallized from ethyl acetate/hexane to yield 6.4 g (65%) of the amide product, mp 140° C.-142° C.

1. temperaturewas cooled in ice
2. filtrationfiltered
3. customevaporated
4. dissolutionThe residual crude acid chloride was redissolved in 85 mL of dichloromethane
5. additionadded dropwise to an ice-
6. temperaturecooled
7. stirringThe mixture was stirred at room temperature for 16 hours
8. washwashed with 0.4N hydrochloric acid, brine, 5% aqueous sodium bicarbonate, and brine again
9. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
10. customevaporated
11. customthe residue recrystallized from ethyl acetate/hexane