Ammonia → 4-Amino-5-bromo-2-chloropyrimidine

HRID 2426276Notes

Reaction equation

HRID 2426276 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH3:10]>C1COCC1>[Br:1][C:2]1[C:3]([NH2:10])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 27632934-Amino-5-bromo-2-chloropyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (25g, 110 mmol) in 200 mL THF is treated with 47 mL of ammonia (330 mmol, 7.0M solution in methanol). After stirring for 15 hours the solution is concentrated under reduced pressure and purified by short-filtration (SiO2, Hexanes: Ethyl acetate/1:1) to yield 21g (92%) of 1 as a white solid.

Workup

  1. concentrationis concentrated under reduced pressure
  2. filtrationpurified by short-filtration (SiO2, Hexanes: Ethyl acetate/1:1)

Sources & evidence

ORD record
ord-1b57774ad68d496e8aeb25ca9f49d7c5
Source dataset
uspto-grants-2011_06
Patent number
US07968557B2

Reaction notes

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