Potassium Carbonate → N-(4-Chloro-5-methylpyrimidin-2-YL)-N-methylmethanesulfonamide

HRID 1694732

Reaction equation

HRID 1694732 reaction equation
[CH3:1][NH:2][SH:3](=[O:5])=[O:4].Cl[C:7]1[N:12]=[C:11]([Cl:13])[C:10]([CH3:14])=[CH:9][N:8]=1.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:13][C:11]1[C:10]([CH3:14])=[CH:9][N:8]=[C:7]([N:2]([CH3:1])[S:3]([CH3:15])(=[O:5])=[O:4])[N:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 178486264HCID 178486264, compound

Product 1

HCID 72211794N-(4-Chloro-5-methylpyrimidin-2-YL)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-methylsulphonamide (3.35 g), 2,4-dichloro-5-methylpyrimidine (5 g) and potassium carbonate (4.3 g) in DMF (50 ml) was heated at 80° C. for 4 h. The reaction was quenched with water (200 ml) and extracted with ethylacetate. The organics were dried, evaporated under reduced pressure and the residue triturated with ether. The solid was filtered off (4-isomer) and the filtrate evaporated under reduced pressure and subjected to RPHPLC to obtain the 2-isomer, yield 0.37 g.

Workup

  1. customThe reaction was quenched with water (200 ml)
  2. extractionextracted with ethylacetate
  3. customThe organics were dried
  4. customevaporated under reduced pressure
  5. customthe residue triturated with ether
  6. filtrationThe solid was filtered off (4-isomer)
  7. customthe filtrate evaporated under reduced pressure
  8. customto obtain the 2-isomer, yield 0.37 g

Sources & evidence

ORD record
ord-86007e06b1a2473aa58df9d9b94b2f1b
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Linked notes

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