Hydrazine → 4-Chloro-6-hydrazinyl-2-(methylsulfanyl)pyrimidine

HRID 2065503

Reaction equation

HRID 2065503 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([S:11][CH3:12])[N:5]=1>ClCCl>[Cl:3][C:4]1[N:5]=[C:6]([S:11][CH3:12])[N:7]=[C:8]([NH:1][NH2:2])[CH:9]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 14845464-Chloro-6-hydrazinyl-2-(methylsulfanyl)pyrimidineYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Referring to Scheme 2, anhydrous hydrazine (164 mg, 162 μl, 5.1 mmol) and dichloromethane (3 ml) were cooled to −78° C. 4,6-Dichloro-2-(methylthio)pyrimidine (1 g, 5.1 mmol) was slowly added. The mixture was allowed to stir for 10 minutes then the bath was replaced with an ice bath and the solution allowed to slowly reach 0° C. The precipitate was filtered and washed with DCM. 1-(6-Chloro-2-(methylthio)pyrimidin-4-yl)hydrazine (624 mg, 64%) was obtained. [M+H] calc'd for C5H7ClN4S, 191; found, 191.

Workup

  1. customthe bath was replaced with an ice bath
  2. customallowed to slowly reach 0° C
  3. filtrationThe precipitate was filtered
  4. washwashed with DCM

Sources & evidence

ORD record
ord-3e14dd27720a428dad453f76d6f57fa7
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Linked notes

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