Methyl iodide → 4,5-Dihydro-4-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 231511Notes

Reaction equation

HRID 231511 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]#[N:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[CH3:25][N:12]1[CH2:11][CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:1])[F:21])[CH:4]=2)[N:14]2[N:15]=[CH:16][C:17]([C:18]#[N:19])=[C:13]12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1357733074,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 145018554,5-Dihydro-4-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile (Ex. 19) and 220 mg of 60% sodium hydride dispersed in mineral oil in 50 ml of N,N-dimethylformamide was stirred at room temperature under nitrogen for 3 1/2 hours. Then one ml of iodomethane was added and the reaction mixture was stirred under nitrogen for 16 hours. The mixture was evaporated in vacuo and gave an oil. The oil crystallized upon trituration in n-hexane to give the product which was recrystallized from ethyl acetate:n-hexane (1:4) and this gave the desired product as yellow crystals, mp 120°-122° C.

Workup

  1. stirringthe reaction mixture was stirred under nitrogen for 16 hours
  2. customThe mixture was evaporated in vacuo
  3. customgave an oil
  4. customThe oil crystallized upon trituration in n-hexane
  5. customto give the product which
  6. customwas recrystallized from ethyl acetate:n-hexane (1:4)

Sources & evidence

ORD record
ord-b707659b2fb544b7af270d9669a7577e
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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