Water → HCID 86621098, compound

HRID 1620867Notes

Reaction equation

HRID 1620867 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[F:7][C:8]([F:24])([F:23])[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=1)[OH:10].[NH2:25][C:26]1[N:31]=[C:30](Cl)[CH:29]=[C:28]([Cl:33])[N:27]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:33][C:28]1[CH:29]=[C:30]([O:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)[C:8]([F:7])([F:23])[F:24])[N:31]=[C:26]([NH2:25])[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 66742969HCID 66742969, compound

Product 1

HCID 86621098HCID 86621098, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Cs2CO3 (325 mg, 1.0 mmol) was added to a solution of 2,2,2-trifluoro-1-[2-(1-methyl-1H-pyrazol-4-yl)-phenyl]-ethanol (60 mg, 0.2 mmol) in 10 ml of anhydrous THF, and the mixture was stirred for 20 minutes. 2-Amino-4,6-dichloro-pyrimidine (32 mg, 0.2 mmol) was added, and then the reaction mixture was heated at 110° C. until the reaction was complete. After cooling, 5 ml of water was added, and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to afford 70 mg of 4-chloro-6-{2,2,2-trifluoro-1-[2-(1-methyl-1H-pyrazol-4-yl)-phenyl]-ethoxy}-pyrimidin-2-ylamine (yield: 92%).

Workup

  1. temperatureAfter cooling
  2. extractionto extract the product
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-e9b81977381e40cc81d6444aa6253181
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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