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

HRID 2260532Notes

Reaction equation

HRID 2260532 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:13]3[NH:14][C:15](=[O:18])[CH2:16][CH2:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1.[CH3:26]I.O>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:13]3[N:14]([CH3:26])[C:15](=[O:18])[CH2:16][CH2:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1361791792-(4-Fluorophenyl)-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Product 1

HCID 199572422-(4-Fluorophenyl)-4-methyl-5-oxo-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidineYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. extractionThe separated oil was extracted with dichloromethane
  3. washthe solution was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained crude solid
  8. customwas recrystallized from a mixture of dichloromethane and diisopropyl ether

Sources & evidence

ORD record
ord-76f78d1e9c3948129b19b72e95f26edb
Source dataset
uspto-grants-1995_12
Patent number
US05478827

Reaction notes

Loading…