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

HRID 2195078Notes

Reaction equation

HRID 2195078 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2[CH:22]=[C:21]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[N:20]=[C:19]([N:29]3[CH2:33][CH2:32][CH2:31][CH:30]3[CH3:34])[N:18]=2)[CH:13]=[CH:14][C:15]=1[F:16].CCN(C(C)C)C(C)C.CC(N(C)C)=O>CCOC(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2[N:18]=[C:19]([N:29]3[CH2:33][CH2:32][CH2:31][CH:30]3[CH3:34])[N:20]=[C:21]([N:23]3[CH2:24][CH2:25][N:26]([C:5]4[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=4)[CH2:27][CH2:28]3)[CH:22]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 57761745HCID 57761745, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Heat a solution of 5-bromo-2-chloropyrimidine (Lancaster Chemicals, 565 mg), 4-(3-chloro-4-fluorophenyl)-2-(2-methylpyrrolidin-1-yl)-6-piperazin-1-yl-pyrimidine (1000 mg), DIEA (500 mg) and DMA (5 mL) at 110° C. for 3 h under nitrogen. Dilute with EtOAc (15 mL), wash with water (3×10 mL), dry (Na2SO4), and evaporate. Purify by silica gel chromatography, eluting with 1:1 hexanes:EtOAc to provide the title compound.

Workup

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

Sources & evidence

ORD record
ord-d84e49d94a354677a973dd21c6c7de03
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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