Diethylamine → {4-(3-Chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-ylmethyl}-diethyl-amine

HRID 230941Notes

Reaction equation

HRID 230941 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:6]=[C:5]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[N:4]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].CC(N(C)C)=O>O>[Cl:15][C:11]1[CH:10]=[C:9]([C:7]2[CH:6]=[C:5]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)[N:4]=[C:3]([CH2:2][N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])[N:8]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 31374DimethylacetamideHCID 577614002-Bromomethyl-4-(3-chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

Product 1

HCID 57761914{4-(3-Chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-ylmethyl}-diethyl-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 2-bromomethyl-4-(3-chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine (32 mg, 0.06 mmol), diethylamine (0.5 mL), DMA (2 mL) and heat at 80° C. for 3 hours. Let cool to room temperature and add water (5 mL). Extract with EtOAc (10 mL), wash with water (10 mL), dry (Na2SO4) and evaporate. Purify by column chromatography (1:1 hexanes/EtOAc) to obtain {4-(3-chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-ylmethyl}-diethyl-amine as a yellow solid.

Workup

  1. extractionExtract with EtOAc (10 mL)
  2. washwash with water (10 mL)
  3. dry with materialdry (Na2SO4)
  4. customevaporate
  5. customPurify by column chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-51865bcb71644be4bff6a78b8950aabc
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

Loading…