Dimethylformamide → 4-(Chloromethyl)-2-(methylthio)pyrimidine

HRID 546555Notes

Reaction equation

HRID 546555 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:13])=O.CN(C)C=O>ClCCl>[Cl:13][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 14270868(2-(Methylthio)pyrimidin-4-yl)methanol

Product 1

HCID 552634394-(Chloromethyl)-2-(methylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 13.69 g of [2-(methylthio)pyrimidin-4-yl]methanol obtained in stage a) in 250 mL of dichloromethane are added dropwise 7.67 mL of thionyl chloride, followed by 3.91 mL of N,N-dimethylformamide. The reaction mixture is stirred at room temperature for 15 hours and concentrated under reduced pressure. The residue is taken up in diisopropyl ether and the solid formed is filtered off and dried to give 10.28 g of 4-(chloromethyl)-2-(methylthio)pyrimidine, the characteristics of which are as follows:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe solid formed
  3. filtrationis filtered off
  4. customdried

Sources & evidence

ORD record
ord-f8f2d38b348844d38df371e58975855b
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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