Thionyl Chloride → 5-Chloromethyl-4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 890420Notes

Reaction equation

HRID 890420 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[C:10]([CH2:11]O)=[CH:9][N:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:6]=1.S(Cl)([Cl:25])=O>ClCCl.CCOCC>[Cl:25][CH2:11][C:10]1[C:5]([CH2:4][CH2:3][O:2][CH3:1])=[N:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 22250821HCID 22250821, compound

Product 1

HCID 219356255-Chloromethyl-4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidineYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.23 g (10.34 mmol) [4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol and 0.788 ml (10.86 mmol) thionylchloride in 30 ml dichloromethane was stirred for 1 h at RT. The reaction mixture was taken up in ether and washed with sodium bicarbonate solution and water. The ether phase was concentrated under reduced pressure to give 3.42 g of pure 5-chloromethyl-4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine.

Workup

  1. washwashed with sodium bicarbonate solution and water
  2. concentrationThe ether phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-baaac49583f94595b9ce7b591cc74df5
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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