2-Bromoethyl methyl ether → 4-[4-(2-Methoxyethyl)piperazin-1-yl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

HRID 2053074Notes

Reaction equation

HRID 2053074 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: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(N(C(C)C)CC)(C)C.Br[CH2:42][CH2:43][O:44][CH3:45].[N-]=C=O>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:45][O:44][CH2:43][CH2:42][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

Participants

6

Reactant 4

HCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 105034IsocyanateHCID 866124954-(Piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

Product 1

HCID 866124964-[4-(2-Methoxyethyl)piperazin-1-yl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 4-(piperazin-1-yl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt (Example 1; 100 mg) and diisopropylethylamine (78 μl) in acetonitrile (3 ml) was added 2-bromoethylmethylether (31 μl). The resulting solution was stirred at room temperature for 16 hrs, followed by heating at 45° C. for 24 hrs. Polymer bound isocyanate (1 mmol/g, 300 mg) was then added and the mixture was shaken at room temperature for 72 hrs before filtering and concentrating in vacuo. Residue was dissolved in dimethylsulphoxide and purified using the prep-HPLC to give 4-[4-(2-methoxyethyl)piperazin-1-yl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile trifluoroacetic acid salt as a white solid (8 mg).

Workup

  1. temperatureby heating at 45° C. for 24 hrs
  2. additionwas then added
  3. stirringthe mixture was shaken at room temperature for 72 hrs
  4. filtrationbefore filtering
  5. concentrationconcentrating in vacuo
  6. dissolutionResidue was dissolved in dimethylsulphoxide
  7. custompurified

Sources & evidence

ORD record
ord-d9e519ac139a4f30ace9fa9727986eeb
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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