Dimethylformamide → 4-[4-(2-Tert-butyloxycarbonylethyl)-piperazin-1-yl]-6-(3-trifluoromethyl-phenyl)pyrimidine-2-carbonitrile
Reaction equation
FC(F)(F)C(O)=O.[N:8]1([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[N:17]=[C:16]([C:30]#[N:31])[N:15]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[CH:33]=[CH2:34].C(N(C(C)C)CC)(C)C.CN(C)C=O>CO>[C:37]([O:36][C:32]([CH2:33][CH2:34][N:11]1[CH2:10][CH2:9][N:8]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)[N:17]=[C:16]([C:30]#[N:31])[N:15]=2)[CH2:13][CH2:12]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
4-(Piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (112 mg), tert-butyl acrylate (49 μl), diisopropylethylamine (59 μl) and dimethylformamide (0.2 ml) were combined and stirred at 45° C. for 16 hrs. After adding methanol, product was purified by using the prep-HPLC to generate 4-[4-(2-tert-butoxycarbonyl-ethyl)-piperazin-1-yl]-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt as a white solid (30 mg).
Workup
- customwas purified
Sources & evidence
- ORD record
- ord-538cbb0dfe2b4e76a435866140a551a8
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326715B2
Reaction notes
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