Methyl iodide → 4-Methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

HRID 2380289Notes

Reaction equation

HRID 2380289 reaction equation
[H-].[Na+].[N:3]1[N:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:6]2=[CH:5][CH:4]=1.CI.[C:14](OCC)(=O)C>CN(C)C=O>[CH3:14][N:11]1[CH2:10][CH2:9][CH2:8][N:7]2[N:3]=[CH:4][CH:5]=[C:6]12

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1356276294H,5H,6H,7H-pyrazolo(1,5-a)pyrimidine

Product 1

HCID 150777434-Methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 62% sodium hydride (1.41 g) in N,N-dimethylformamide (30 ml) was added 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (4.5 g) under ice-cooling. To this solution was added dropwise methyl iodide (2.27 ml) under ice-cooling, and the mixture was stirred at the same temperature for 1.5 hours. The reaction mixture was poured into ethyl acetate (50 ml), and the resulting precipitate was filtered off. The filtrate was evaporated to give 4-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (5.05 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationthe resulting precipitate was filtered off
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-27438b75cbf948a0ae7430f12ffc8ab0
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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