Thionyl Chloride → [Rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1242329Notes

Reaction equation

HRID 1242329 reaction equation
[CH:1]1([C:4]2[C:9]([CH:10](O)[CH2:11][CH2:12][CH3:13])=[CH:8][N:7]=[C:6]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:5]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:27])=O>ClCCl>[Cl:27][CH:10]([C:9]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=2)=[N:7][CH:8]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935774[Rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butan-1-ol

Product 1

HCID 21935892[Rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 392 mg (1.17 mmol) [rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-butan-1-ol and 0.09 ml (1.22 mmol) thionylchloride in 4 ml dichloromethane were stirred at RT for 1 h. After concentration under reduced pressure 421 mg of pure [rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine was isolated.

Workup

  1. concentrationAfter concentration under reduced pressure 421 mg of pure [rac]-5-(1-chloro-butyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine
  2. customwas isolated

Sources & evidence

ORD record
ord-04f4babd96344c1ea3f2659cc902755f
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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