Potassium Carbonate → 4-Chloro-6-methoxyamino-2-methylsulfonylpyrimidine

HRID 1198100Notes

Reaction equation

HRID 1198100 reaction equation
Cl.[CH3:2][O:3][NH2:4].[Cl:5][C:6]1[CH:11]=[C:10](Cl)[N:9]=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[N:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:5][C:6]1[CH:11]=[C:10]([NH:4][O:3][CH3:2])[N:9]=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidineHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 191039324-Chloro-6-methoxyamino-2-methylsulfonylpyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

40 g (0.48 mol) of O-methylhydroxylamine hydrochloride is added to a solution of 100 g (0.44 mol) of 4,6-dichloro-2-methylsulfonylpyrimidine in 400 ml of N,N-dimethylformamide. 66 g (0.48 mol) of potassium carbonate is added and the whole is heated at 90° C. for 10 hours. The mixture is allowed to cool, is evaporated down, the residue is taken up in 10% strength aqueous hydrochloric acid and dichloromethane, the phases are separated, dried and concentrated in a rotary evaporator. The 4-chloro-6-methoxyamino-2-methylsulfonylpyrimidine obtained as byproduct may be separated by chromatography on silica gel (developer: cyclohexane/ethyl acetate). There is obtained 39 g (45%) of the title compound as a white crystalline mass of m.p. 135° C.

Workup

  1. temperatureto cool
  2. customis evaporated down
  3. customthe phases are separated
  4. customdried
  5. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-5fd1e429576f41b398f93b1121a299a0
Source dataset
uspto-grants-1994_01
Patent number
US05280009

Reaction notes

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