Ammonium Hydroxide → 6-Chloro-5-fluoropyrimidin-4-amine

HRID 2366232Notes

Reaction equation

HRID 2366232 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[OH-].[NH4+:11]>C(O)CCC>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH2:11])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 112866754,6-Dichloro-5-fluoropyrimidine

Product 1

HCID 534879696-Chloro-5-fluoropyrimidin-4-amineYield 89%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4,6-dichloro-5-fluoro-pyrimidine (1.67 g, 10.0 mmol), n-butanol (6 mL) and 28% ammonium hydroxide (12 mL) in a sealed tube was heated at 90° C. for 2 hours. The precipitated white crystals were collected by filtration to give the desired compound (1.31 g, 89% yield). LCMS (ESI) m/z: 147.9 [M+H+].

Workup

  1. filtrationThe precipitated white crystals were collected by filtration

Sources & evidence

ORD record
ord-455ee7ee94dd4f219cf0ceb917732567
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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