Sodium Iodide → 4-(4-Isopropyl-piperazin-1-yl)-6-(trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N:8]1([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22](C(F)(F)F)[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.[CH:32](N(C(C)C)CC)([CH3:34])[CH3:33].BrC(C)C.[I-].[Na+]>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:32]([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]=[CH:22][C:21]=3[C:2]([F:7])([F:6])[F:1])[N:17]=[C:16]([C:30]#[N:31])[N:15]=2)[CH2:13][CH2:12]1)([CH3:34])[CH3:33]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a solution of 4-(piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (Example 1; 50 mg) in acetonitrile (1 ml) was added diisopropylethylamine (39 μl) and 2-bromopropane (15.5 μl). The resulting solution was subjected to microwave heating at 150° C. for 5 mins. Sodium iodide (2 mg) was added and the reaction mixture was subjected to further heating at 180° C. for 30 mins. Reaction mixture was concentrated in vacuo and the residue was dissolved in methanol and purified using the prep-HPLC to give 4-(4-isopropyl-piperazin-1-yl)-6-(trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (10 mg).
Workup
- temperatureto further heating at 180° C. for 30 mins
- customReaction mixture
- concentrationwas concentrated in vacuo
- dissolutionthe residue was dissolved in methanol
- custompurified
Sources & evidence
- ORD record
- ord-aa9bb46af4284868b0fe847878f56d98
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326715B2
Reaction notes
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