Pyridine → 2-methylthio-5-(2-chloroethyl)-3,6-dimethyl-3H-pyrimidin-4-one

HRID 2222280Notes

Reaction equation

HRID 2222280 reaction equation
[CH3:1][S:2][C:3]1[N:8]([CH3:9])[C:7](=[O:10])[C:6]([CH2:11][CH2:12]O)=[C:5]([CH3:14])[N:4]=1.N1C=CC=CC=1.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[CH3:1][S:2][C:3]1[N:8]([CH3:9])[C:7](=[O:10])[C:6]([CH2:11][CH2:12][Cl:23])=[C:5]([CH3:14])[N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 693142522-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one

Product 1

HCID 693164112-methylthio-5-(2-chloroethyl)-3,6-dimethyl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-methylthio-5-(2-hydroxyethyl)-3,6-dimethyl-3H-pyrimidin-4-one (20.3 g, 0.095 mol) in chloroform (200 ml) was added one equivalent of pyridine (7.6 ml), followed by slow addition of three equivalents of thionyl chloride (21 ml). After stirring for 15 minutes, the mixture was concentrated and water (300 ml) was added. The precipitate was collected and washed with water, isopropyl alcohol and petroleum ether. Yield 34.4 g (64%). Yield 20.3 g (92%). Mp. 135-137° C.

Workup

  1. concentrationthe mixture was concentrated
  2. additionwater (300 ml) was added
  3. customThe precipitate was collected
  4. washwashed with water, isopropyl alcohol and petroleum ether

Sources & evidence

ORD record
ord-2c166629aba74578a74367b6725b4103
Source dataset
uspto-grants-2008_05
Patent number
US07371769B2

Reaction notes

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