Ethanol → 2-Methyl-5-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1726999Notes

Reaction equation

HRID 1726999 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[N:10][C:11]([CH3:14])=[N:12][CH:13]=1.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(O)C>O.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:11]1[N:10]=[CH:9][C:8]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)=[CH:13][N:12]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 143877445-Bromo-2-methylpyrimidine

Product 1

HCID 219359462-Methyl-5-(4-trifluoromethyl-phenyl)-pyrimidineYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7.95 g (75 mmol) of sodium carbonate in 15 ml of water was added to a mixture of 2.6 g (15 mmol) of 5-bromo-2-methylpyrimidine (Coll. Czech. Chem. Comm. 14 (1949), 223-235), of 4 g (21 mmol) of 4-(trifluoromethyl)benzene boronic acid and of 0.52 g (0.45 mmol) of tetrakis(triphenylphosphine)palladium in a mixture of 50 ml of 1,2-dimethoxy-ethane and of 30 ml of ethanol. The mixture was stirred at 80° C. for 2 hours, afterwards, it was concentrated by distilling off the major part of the organic solvents. Subsequently, the residue was extracted with 3 portions of tert.-butyl methyl ether. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and finally evaporated. The residue was chromatographed on silicagel with a mixture of dichloromethane/tert.-butyl methyl ether (9/1 vol./vol.) as eluent. 3 g of the title compound were obtained as greenish solid. MS: 239.2 (M+H)+.

Workup

  1. concentrationafterwards, it was concentrated
  2. distillationby distilling off the major part of the organic solvents
  3. extractionSubsequently, the residue was extracted with 3 portions of tert.-butyl methyl ether
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customfinally evaporated
  7. customThe residue was chromatographed on silicagel with a mixture of dichloromethane/tert.-butyl methyl ether (9/1 vol./vol.) as eluent

Sources & evidence

ORD record
ord-29c030a69b204ce4a0b9e655c2c11fac
Source dataset
uspto-grants-2009_02
Patent number
US07495001B2

Reaction notes

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