Ammonium Hydroxide → Pyrimidine, 4-amino-6-chloro-2,5-dimethyl-

HRID 868952

Reaction equation

HRID 868952 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[N:3]=1.[OH-].[NH4+:12]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]=[C:6]([NH2:12])[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 2370134,6-Dichloro-2,5-dimethylpyrimidine

Product 1

HCID 205584Pyrimidine, 4-amino-6-chloro-2,5-dimethyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A microwave vial was charged with 4,6-dichloro-2,5-dimethylpyrimidine (523 mg, 2.95 mmol) and ammonium hydroxide (8 mL) in ethanol (4 mL). The vial was heated to 80° C. and stirred for 8 h. After concentration under reduced pressure, the reaction mixture was extracted with EtOAc (15 mL×8). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give 6-chloro-2,5-dimethylpyrimidin-4-amine as a yellow solid (411 mg). MS (ESI): m/z 158 [M+H]+.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. extractionthe reaction mixture was extracted with EtOAc (15 mL×8)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea626cb6c9be42e284ebcf6abfc8c613
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

Loading…