Formic Acid → 6,7-Dihydropyrazolo[1,5-a]pyrimidine-4(5H)-carbaldehyde

HRID 1681649Notes

Reaction equation

HRID 1681649 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[N:11]1[N:15]2[CH2:16][CH2:17][CH2:18][NH:19][C:14]2=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH:5]([N:19]1[CH2:18][CH2:17][CH2:16][N:15]2[N:11]=[CH:12][CH:13]=[C:14]12)=[O:7]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 1356276294H,5H,6H,7H-pyrazolo(1,5-a)pyrimidine

Product 1

HCID 150777426,7-Dihydropyrazolo[1,5-a]pyrimidine-4(5H)-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To acetic anhydride (0.153 ml) was added formic acid (0.077 ml) at 15-20° C. The mixture was stirred at ambient temperature for 30 minutes. To this solution was added 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (100 mg) under ice-cooling and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added to a mixture of dichloromethane and aqueous sodium bicarbonate solution. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo to give 4-formyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (79.9 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. dry with materialThe separated organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-67ca3f84fc8f4cc28f0e1d1d5876d3e7
Source dataset
uspto-grants-1992_12
Patent number
US05173485

Reaction notes

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