Hydrazine hydrate (1:1) → 5-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide

HRID 2267421Notes

Reaction equation

HRID 2267421 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.O.[NH2:14][NH2:15]>C1COCC1.O>[Cl:1][C:2]1[C:3]([C:10]([NH:14][NH2:15])=[O:12])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 7257115-Chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid

Product 1

HCID 432447685-Chloro-2-(methylthio)pyrimidine-4-carbohydrazideYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid (4.0 g, 19.6 mmol) and 1,1-carbonyl diimidazole (6.35 g, 39.2 mmol) were dissolved in 80 mL THF and stirred at room temperature. After 3 h, the solution was cooled in an ice bath and hydrazine hydrate (1.90 mL, 39.2 mmol) was added in one quick portion. The solution was allowed to stir for 5 h, gradually warming to room temperature. The reaction mixture was diluted with excess H2O and extracted with EtOAc several times. These organics were combined and washed with 2 N HCl. The combined aqueous layers were then basified carefully with 5 N NaOH, and extracted once again with EtOAc. This second set of organic layers was combined, dried over magnesium sulfate and concentrated under vacuum to give 2.46 g (58% yield) of product as a white solid. MS (M+H)+ 219.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. stirringto stir for 5 h
  3. temperaturegradually warming to room temperature
  4. extractionextracted with EtOAc several times
  5. washwashed with 2 N HCl
  6. extractionextracted once again with EtOAc
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ebd15e7726f34cc9a7db4ba5a871c6a2
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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