Water → 2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

HRID 2382641Notes

Reaction equation

HRID 2382641 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Cl:12][C:13]1[N:18]=[C:17](Cl)[C:16]([Cl:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:12][C:13]1[N:18]=[C:17]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([NH:6][CH3:7])=[O:5])[C:16]([Cl:20])=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 3080722-Amino-N-methylbenzamide

Product 1

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 15.0 g (99.8 mmol) of 2-amino-N-methyl-benzamide in DMF (300 mL) are added 2,4,5-trichloropyrimidine (23.8 g, 130 mmol) and potassium carbonate (17.9 g, 130 mmol). The reaction mixture is stirred at 75° C. for 5 hours, cooled to room temperature, and then poured into H2O (600 mL). The resulting precipitate is collected by a filtration followed by washing with 50% aqueous CH3CN (200 mL) and dried under reduced pressure (40° C., 10 hours) to give desired 2-(2,5-dichloro-pyrimidin-4-yl-amino)-N-methyl-benzamide as ivory solid (26.4 g, 88.9 mmol, 89%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate is collected by a filtration
  3. washby washing with 50% aqueous CH3CN (200 mL)
  4. customdried under reduced pressure (40° C., 10 hours)

Sources & evidence

ORD record
ord-9f332fb9d8a04961957e3142a13b3fe3
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

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