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

HRID 230945Notes

Reaction equation

HRID 230945 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[CH:5]=[C:4]([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:3]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[C:4]([N:16]3[CH2:17][CH2:18][N:19]([C:22]4[C:27]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:20][CH2:21]3)[N:3]=[C:2]([N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])[N:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 577614902-Chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

Product 1

HCID 57761560{4-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-yl}-diethyl-amine

Conditions

Temperature
60 °C

Procedure

Combine a mixture of 2-chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine (47 mg, 1 mmol) and diethylamine (2 mL). Heat the mixture in a sealed tube at 60° C. for 16 hours. Cool to room temperature and evaporate. Add 1 M NaOH (1 mL) and extract 2× with EtOAc (2 mL each). Combine the organic layers, dry (Na2SO4), and purify using preparative TLC (9:1 hexanes/EtOAc) to obtain {4-(3-Chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-yl}-diethyl-amine as a white solid.

Workup

  1. temperatureCool to room temperature
  2. customevaporate
  3. additionAdd 1 M NaOH (1 mL)
  4. extractionextract 2× with EtOAc (2 mL each)
  5. dry with materialCombine the organic layers, dry (Na2SO4)
  6. custompurify

Sources & evidence

ORD record
ord-cef276283da54bf283f523131c47e84f
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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