Hydrazine hydrate (1:1) → Pyrimidine-2-carbohydrazide

HRID 513217Notes

Reaction equation

HRID 513217 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=O.O.[NH2:12][NH2:13]>CCO>[N:6]1[CH:7]=[CH:8][CH:9]=[N:10][C:5]=1[C:3]([NH:12][NH2:13])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 36138712-Pyrimidinecarboxylic acid, methyl ester

Product 1

HCID 11182639Pyrimidine-2-carbohydrazideYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of methylpyrimidine-2-carboxylate (1.0 g, 7.2 mmol) in EtOH (5.6 mL) was added hydrazine monohydrate (0.72 mL, 14 mmol). The reaction mixture became homogeneous and after 5 min a precipitate formed. Stirring was continued for 1 h. The mixture was filtered, and the collected solid was washed with additional EtOH to provide the desired product as a beige solid (720 mg, 72%). MS (ESI): mass calcd. C5H6N4O, 138.1; m/z found, 139.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 10.06 (s, 1H), 8.92 (d, J=4.9 Hz, 2H), 7.64 (t, J=4.9 Hz, 1H), 4.64 (s, 2H).

Workup

  1. customa precipitate formed
  2. waitwas continued for 1 h
  3. filtrationThe mixture was filtered
  4. washthe collected solid was washed with additional EtOH

Sources & evidence

ORD record
ord-3e47f3d2fd4a403b8b6d25999b4b981f
Source dataset
uspto-grants-2015_08
Patent number
US09102686B2

Reaction notes

Loading…