Hydrogen Bromide → 2-Bromomethyl-4-(3-chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

HRID 230940Notes

Reaction equation

HRID 230940 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]4[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:16][CH2:15]3)[N:11]=[C:10]([CH2:30]OC)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[BrH:33]>CC(O)=O>[Br:33][CH2:30][C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:13]=[C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[N:11]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 577611754-(3-Chloro-phenyl)-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Stir a mixture of 4-(3-chloro-phenyl)-2-methoxymethyl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine in a solution of 30% HBr in HOAc (25 mL) at 60° C. for 3 hours. Evaporate the mixture, adjust the pH to basic with 1M NaOH, and collect a tan solid. Purify by liquid chromatography (3:1 hexanes/EtOAc) to obtain 2-bromomethyl-4-(3-chloro-phenyl)-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidine as a yellow solid.

Workup

  1. customEvaporate the mixture
  2. customcollect a tan solid
  3. customPurify by liquid chromatography (3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-9a9d6b0ef2764e6fb7194b6d23205111
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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