3-(Trifluoromethyl)benzaldehyde → HCID 89445371, compound

HRID 632728Notes

Reaction equation

HRID 632728 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:20])=[N:10][CH:11]=[N:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.C[Si]([C:37]#[N:38])(C)C>C(#N)C>[NH2:20][C:9]1[N:10]=[CH:11][N:12]=[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH:26]([C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([C:22]([F:32])([F:31])[F:21])[CH:24]=3)[C:37]#[N:38])[CH2:16][CH2:15]2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 82115Trimethylsilyl cyanideHCID 89442443HCID 89442443, compound

Product 1

HCID 89445371HCID 89445371, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask equipped with a stir bar was dissolved 5-(4-Fluoro-phenyl)-6-piperazin-1-yl-pyrimidin-4-ylamine (1 eq) and 3-trifluoromethyl-benzaldehyde (1.05 eq) in acetonitrile. The vial was sealed with a rubber septa, then evacuated and backfilled with argon. To this sealed vessel was added trimethylsilyl cyanide (1.05 eq) and the reaction was allowed to stir at room temperature until complete. The reaction is quenched by addition of an equal amount of ammonium chloride (saturated, aqueous solution), then extracted with ethyl acetate. The organic layers are then dried over sodium sulfate, filtered and concentrated to give the title compound. LC-MS: (M+1=457, obsd.=457).

Workup

  1. customIn a round bottom flask equipped with a stir bar
  2. customThe vial was sealed with a rubber septa
  3. customevacuated
  4. customThe reaction is quenched by addition of an equal amount of ammonium chloride (saturated, aqueous solution)
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layers are then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-39c2c078c0af47019cf0441dbfaf624f
Source dataset
uspto-grants-2016_04
Patent number
US09321760B2

Reaction notes

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