Formic Acid → N-(5-Amino-1-methyl-1H-pyrazol-4-yl)formamide

HRID 1247807Notes

Reaction equation

HRID 1247807 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:8]=[N:9][N:10]([CH3:13])[C:11]=1[NH2:12].[C:14](OC(=O)C)(=[O:16])C.C(O)=O>C(N(CC)CC)C.[Cl-].[Na+].O>[NH2:12][C:11]1[N:10]([CH3:13])[N:9]=[CH:8][C:7]=1[NH:6][CH:14]=[O:16]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 21904554N-(5-Amino-1-methyl-1H-pyrazol-4-yl)formamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 4,5-diamino-1-methylpyrazole sulfuric acid salt (20 g) in triethylamine (29.2 ml) was stirred at 0° C. for 10 minutes. A mixture of acetic anhydride (9.87 ml) and formic acid (7.96 ml) was stirred at 40° C. for 30 minutes, cooled to 0° C., and added dropwise to the above solution at 0° C. The whole mixture was stirred at 0° C. for 2 hours. To the mixture was added brine, and the whole mixture was extracted with tetrahydrofuran. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give crude N-(5-amino-1-methyl-1H-pyrazol-4-yl)formamide, which was used in the next step without further purification.

Workup

  1. stirringwas stirred at 40° C. for 30 minutes
  2. temperaturecooled to 0° C.
  3. additionadded dropwise to the above solution at 0° C
  4. stirringThe whole mixture was stirred at 0° C. for 2 hours
  5. extractionthe whole mixture was extracted with tetrahydrofuran
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7a1d28e7c4424b3c85dbc0e414cf83ff
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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