Methanol → 2-Chloro-4-hydrazinylpyrimidine

HRID 1465889Notes

Reaction equation

HRID 1465889 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][NH2:10].CO.C(Cl)Cl>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][NH2:10])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 9321HydrazineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 160921982-Chloro-4-hydrazinylpyrimidineYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,4-dichloropyrimidine (2.0 g) in EtOH (25 mL) was cooled to 0-20° C. and treated with hydrazine (2.8 mL). The progress of the reaction was followed by TLC using 10% MeOH:CH2Cl2 as mobile phase and visualizing under UV light. The mixture was concentrated under reduced pressure to afford 3.1 g of crude 2-chloro-4-hydrazinyl-pyrimidine (yield=94.8%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93bb99dcb09a43b59a21515d873991cd
Source dataset
uspto-grants-2015_04
Patent number
US08999996B2

Reaction notes

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