Pyrazolo(1,5-a)pyrimidine-3-carbonitrile → 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 231518Notes

Reaction equation

HRID 231518 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]2=[C:3]([C:10]#[N:11])[CH:2]=1.[BH4-].[Na+]>CO>[N:1]1[N:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:4]2=[C:3]([C:10]#[N:11])[CH:2]=1

Participants

4

Reactant 2

HCID 819275Pyrazolo(1,5-a)pyrimidine-3-carbonitrileHCID 4311764Sodium borohydride

Product 1

HCID 1356713724,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 42.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 4.0 g of pyrazolo[1,5-a]-pyrimidine-3-carbonitrile in 200 ml of methyl alcohol under nitrogen at, room temperature, was added, one at a time, 3 pellets of sodium borohydride. The mixture was stirred for several hours and then was allowed to stand at room temperature. The product was collected by filtration to give 1.75 g of 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile, mp 206°-207° C.

Workup

  1. additionwas added
  2. customto stand at room temperature
  3. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-5ca1c1690f7d49e9a1dc6efbd26ea0b6
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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