2-{4-[6-(3-Chloro-4-fluorophenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-5-bromopyrimidine → 2-{4-[6-(3-Chloro-4-fluorophenyl)-2-(2-methylpyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyrimidine-5-carbonitrile

HRID 2195079Notes

Reaction equation

HRID 2195079 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH:16]3[CH3:20])[N:12]=[C:11]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30](Br)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[C:34]([Cu])#[N:35]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH:16]3[CH3:20])[N:12]=[C:11]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([C:34]#[N:35])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 577617682-{4-[6-(3-Chloro-4-fluorophenyl)-2-(2-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-5-bromopyrimidineHCID 178418546HCID 178418546, compound

Product 1

HCID 577620032-{4-[6-(3-Chloro-4-fluorophenyl)-2-(2-methylpyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Heat a mixture of 2-{4-[6-(3-chloro-4-fluorophenyl)-2-(2-methylpyrrolidin-1-yl)-pyrimidin-4-yl]-piperazin-1-yl}-5-bromopyrimidine (478 mg) and CuCN (270 mg) in DMF at 150° C. for 16 h in a round bottom flask that is open to the air. Let cool, dilute with EtOAc (15 mL), wash with water (3×10 mL), dry (Na2SO4), and evaporate. Purify by silica gel chromatography, eluting with 3:1 hexanes:EtOAc to provide the title compound.

Workup

  1. temperatureHeat
  2. temperatureLet cool
  3. washwash with water (3×10 mL)
  4. dry with materialdry (Na2SO4)
  5. customevaporate
  6. customPurify by silica gel chromatography
  7. washeluting with 3:1 hexanes

Sources & evidence

ORD record
ord-687a83ae48554124b1cbff7601188bca
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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