Ammonium Hydroxide → 4-Amino-5-bromo-2-chloropyrimidine

HRID 1619124Notes

Reaction equation

HRID 1619124 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[NH4+:11]>CO>[Br:1][C:2]1[C:3]([NH2:11])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 27632934-Amino-5-bromo-2-chloropyrimidineYield 79.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-bromo-2,4-dichloropyrimidine (8.54 g, 37.48 mmol) in methanol (12 mL) was added dropwise over 10 minutes to an ice-bath cooled solution of 7M ammonium hydroxide (60 mL, 420 mmol) in methanol (60 mL) and the resulting solution was stirred at room temperature for 24 hours. The mixture was concentrated and water was added. The solid was filtered and dried under reduced pressure to give the title compound (6.23 g, 73%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater was added
  3. filtrationThe solid was filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f8a75da5bee046e58925d78fbbd26350
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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