Water → HCID 86614295, compound

HRID 469846Notes

Reaction equation

HRID 469846 reaction equation
[H-].[Na+].[CH:3]1([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[C:18]([Cl:23])[N:17]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:23][C:18]1[CH:19]=[C:20]([O:14][CH:9]([CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[C:10]([F:12])([F:13])[F:11])[N:21]=[C:16]([NH2:15])[N:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidineHCID 109430921-cyclohexyl-2,2,2-trifluoroethan-1-ol

Product 1

HCID 86614295HCID 86614295, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

NaH (80 mg, 60%, 3.0 mmol) was added to the solution of 1-cyclohexyl-2,2,2-trifluoro-ethanol (182 mg, 1 mmol) in 10 ml of anhydrous THF, the mixture was stirred for 20 minutes, 2-amino-4,6-dichloro-pyrimidine (164 mg, 1 mmol) was added and then the reaction mixture was heated at 70° C. for 1 hour. After cooling, 5 ml 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 give 202 mg of 4-chloro-6-[1-cyclohexyl-2,2,2-trifluoro-ethoxy]-pyrimidin-2-ylamine, yield 65%.

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-4c9551c718a7416c9d87eff844f026ff
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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