Реакция #83225

Уравнение реакции

water

methyl iodide

sodium hydride

2-(4-fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

→

2-(4-fluorophenyl)-4-methyl-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Выход 68.9%

Растворители

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 2 hours
2. 2
   ЭкстракцияThe separated oil was extracted with dichloromethane
3. 3
   Промывкаthe solution was washed with brine
4. 4
   Другоеdried
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue was purified by column chromatography on silica gel
7. 7
   Другоеthe obtained crude solid
8. 8
   Другоеwas recrystallized from a mixture of dichloromethane and diisopropyl ether

Методика

To a suspension of sodium hydride (60% dispersion in mineral oil, 35 mg) in dry N,N-dimethylformamide (5 ml) was added a solution of 2-(4-fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (250 mg) in dry N,N-dimethylformamide (3 ml) dropwise under ice cooling. The mixture was stirred for 30 minutes and to the mixture was added a solution of methyl iodide (125 mg) in dry N,N-dimethylformamide (2 ml). The mixture was stirred at ambient temperature for 2 hours and poured into water. The separated oil was extracted with dichloromethane and the solution was washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel and the obtained crude solid was recrystallized from a mixture of dichloromethane and diisopropyl ether to give 2-(4-fluorophenyl)-4-methyl-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (180 mg).

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