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

HRID 2234831

Reaction equation

HRID 2234831 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-d6b48ad051694d7791a681db44955dba
Source dataset
uspto-grants-2010_05
Patent number
US07713973B2

Linked notes

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