Benzene, 1-bromo-2-(trifluoromethyl)- → 4-(3-Benzyloxy-propyl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

HRID 733185Notes

Reaction equation

HRID 733185 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([Sn](C)(C)C)[N:15]=[C:14]([C:22]#[N:23])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1Br)([F:27])[F:26]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([C:25]([F:27])([F:26])[F:24])[CH:29]=2)[N:15]=[C:14]([C:22]#[N:23])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 578391104-(3-Benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile

Product 1

HCID 578391144-(3-Benzyloxy-propyl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(3-benzyloxy-propyl)-6-trimethylstannanyl-pyrimidine-2-carbonitrile (100 mg), trifluoromethylbromobenzene (36□μL) and 1,1′-(bistriphenylphosphino)ferrocenedichloropalladium(II) (16 mg) in dimethylformamide (5 mL) was heated in microwave at 150° C. for 5 min. The resulting suspension was diluted with ethyl acetate and water (20 mL), the organic layer being separated, dried over sodium sulphate and evaporated at reduced pressure. Flash silica chromatography afforded 4-(3-benzyloxy-propyl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile as a yellow gum (47 mg).

Workup

  1. customthe organic layer being separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-8996478be43943e783160332716c8d63
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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