Carbon Dioxide → 5-Chloro-2-(methylthio)pyrimidine

HRID 1413043Notes

Reaction equation

HRID 1413043 reaction equation
[Cl:1][C:2]1[C:3](C(O)=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.C(=O)=O>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 280Carbon DioxideHCID 7257115-Chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid

Product 1

HCID 47370635-Chloro-2-(methylthio)pyrimidineYield 89.2%

Procedure

5-Chloro-2-methylthio-4-pyrimidine carboxylic acid (30 g) was heated at 180°-200° C. until all the solid had melted and the evolution of carbon dioxide had ceased (5 min). The residue was allowed to cool and then washed with several portions of chloroform. The chloroform washings were filtered to remove dark insoluble material and the filtrate was concentrated to give 5-chloro-2-methylthiopyrimidine as a pale brown crystalline solid (21 g, 89%), m.p. 55° C.

Workup

  1. custom(5 min)
  2. temperatureto cool
  3. washwashed with several portions of chloroform
  4. filtrationThe chloroform washings were filtered
  5. customto remove dark insoluble material
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-97f3674f964e4f6c8af28d78938cc3ec
Source dataset
uspto-grants-1981_02
Patent number
US04248618

Reaction notes

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