Thionyl Chloride → 5-Chloromethyl-4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1242458Notes

Reaction equation

HRID 1242458 reaction equation
[CH:1]1([C:4]2[C:9]([CH2:10]O)=[C:8]([CH2:12][O:13][CH3:14])[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][CH2:10][C:9]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)=[N:7][C:8]=1[CH2:12][O:13][CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935658HCID 21935658, compound

Product 1

HCID 219357905-Chloromethyl-4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.29 g (3.8 mmol) [4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol in 12 ml dichloromethane was treated with 0.29 ml (3.99 mmol) thionylchloride. After 2 h stirring at RT, the mixture was partitioned between ether and water. The ether-phase was concentrated under reduced pressure giving 1.35 g pure crystalline 5-chloromethyl-4-cyclopropyl-6-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine.

Workup

  1. customthe mixture was partitioned between ether and water
  2. concentrationThe ether-phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd3d7805340d437c95b8626a185a1afa
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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