Hydrazine hydrate (1:1) → 4-Chloro-6-hydrazinylpyrimidine

HRID 220092

Reaction equation

HRID 220092 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.O.[NH2:10][NH2:11]>CC(O)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH:10][NH2:11])[CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 709434,6-Dichloropyrimidine

Product 1

HCID 2472224-Chloro-6-hydrazinylpyrimidineYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4,6-dichloro-pyrimidine (18.68 g, 125 mmol), hydrazine monohydrate (18.28 mL, 376 mmol), and 2-propanol (300 mL) was stirred at room temperature for 3 hours. The reaction mixture was concentrated, triturated with water, and filtered. The solid was washed with water, air-dried to give (6-chloro-pyrimidin-4-yl)-hydrazine (16.97 g, Yield 94%): 1H NMR 400 MHz (d6-DMSO) δ 8.83 (s, 1H), 8.17 (s, 1H), 6.76 (s, 1H), 4.50 (s, 2H); MS m/z 145.02 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customair-dried

Sources & evidence

ORD record
ord-6203da0ef3b845a3a7b5292d779c13c8
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Linked notes

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