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

HRID 576702Notes

Reaction equation

HRID 576702 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]([O:9]C)=O.O.[NH2:12][NH2:13]>CCO>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[C:7]([NH:12][NH2:13])=[O:9]

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 methyl pyrimidine-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. for C5H6N4O, 138.1; m/z found, 139.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 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-08187c705738492dae102ee68683bd7d
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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