Thionyl Chloride → 5-Chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1242471Notes

Reaction equation

HRID 1242471 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[C:10]([CH2:11]O)=[C:9]([CH3:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[N:6]=1.S(Cl)([Cl:26])=O>C(Cl)Cl>[Cl:26][CH2:11][C:10]1[C:5]([CH2:4][CH2:3][O:2][CH3:1])=[N:6][C:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[N:8][C:9]=1[CH3:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935907[4-(2-Methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol

Product 1

HCID 219357495-Chloromethyl-4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidineYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.47 g (7.48 mmol) [4-(2-methoxy-ethyl)-6-methyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol in 25 ml Methylenchloride was treated with 0.57 ml (7.85 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 2.42 g pure 5-chloromethyl-4-(2-methoxy-ethyl)-6-methyl-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-5f8935a80e814d3e8698ef6bab2c732b
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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