Potassium Carbonate → N-[4-(morpholin-4-ylsulfonyl)phenyl]-4-[4-(trifluoromethyl)phenyl]-pyrimidin-2-amine

HRID 1715689Notes

Reaction equation

HRID 1715689 reaction equation
[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([NH2:19])=[NH:18])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN(C)/[CH:22]=[CH:23]/[C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN1CCCN(C)C1=O.O>[N:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]3[N:19]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][CH:27]=4)[CH:23]=[CH:22][N:18]=3)=[CH:14][CH:15]=2)(=[O:8])=[O:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5714026(2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-oneHCID 178512580HCID 178512580, compound

Product 1

HCID 11655630N-[4-(morpholin-4-ylsulfonyl)phenyl]-4-[4-(trifluoromethyl)phenyl]-pyrimidin-2-amineYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
107.5 °C

Procedure

A mixture of N-[4-(morpholin-4-ylsulfonyl)phenyl]guanidine (85 mg, 0.3 mmol), (2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one (43 mg, 0.18 mmol), and potassium carbonate (83 mg, 0.6 mmol) in 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) is stirred at 105 to 110° C. for 18 hrs. It is then cooled to room temperature, and diluted with water (15 ml). The resulting suspension is filtered, and the precipitate is washed with dilute citric acid and water, and then dissolved in ethyl acetate. The organic solution is passed through a pad of silica gel, and the filtrate is evaporated. The residue is triturated with a mixture of methylene chloride and hexanes to give 63 mg of a yellow solid; mp 240-241° C.; MS (ESI) m/z 465.2 (M+H); HRMS: calcd for C21H19F3N4O3S, 464.1130; found (ESI_FT), 465.11835.

Workup

  1. temperatureIt is then cooled to room temperature
  2. filtrationThe resulting suspension is filtered
  3. washthe precipitate is washed with dilute citric acid and water
  4. dissolutiondissolved in ethyl acetate
  5. customthe filtrate is evaporated
  6. customThe residue is triturated with a mixture of methylene chloride and hexanes

Sources & evidence

ORD record
ord-0b0d4f273cff466faee6c796ac61db78
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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