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

HRID 1242325Notes

Reaction equation

HRID 1242325 reaction equation
[CH:1]1([C:4]2[C:9]([CH:10](O)[CH3:11])=[CH:8][N:7]=[C:6]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[N:5]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:25])=O>ClCCl>[Cl:25][CH:10]([C:9]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:5][C:6]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=2)=[N:7][CH:8]=1)[CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935779[Rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol

Product 1

HCID 21935642[Rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidineYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 357 mg (1.16 mmol) [rac]-1-[4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-ethanol and 0.09 ml (1.22 mmol) thionylchloride in 4 ml dichloromethane were stirred for 1 h at RT. The reaction mixture was concentrated under reduced pressure to provide 390 mg of pure [rac]-5-(1-chloro-ethyl)-4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb340c30aeca4ce8b5fa56f90d7609ef
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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