4-Chloro-2-methylthiopyrimidine → 4-Fluoro-2-(methylsulfanyl)pyrimidine

HRID 9760

Reaction equation

HRID 9760 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F-:10].[K+]>COCCOCCOCCOCCOC.C1OCCOCCOCCOCCOCCOC1>[F:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

5

Reactant 2

HCID 971134-Chloro-2-methylthiopyrimidineHCID 522689Potassium Fluoride

Product 1

HCID 102612444-Fluoro-2-(methylsulfanyl)pyrimidineYield 63.1%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8925TetraglymeSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 35.7 g (0.22 mol) of 4-chloro-2-methylthiopyrimidine (Aldrich Chemical Co., Milwaukee, Wis., USA) in 135 mL of tetraglyme was added 18-crown-6 (1.33 g) and potassium fluoride (Anhydrous, Aldrich Chemical Co., Milwaukee, Wis., USA, 80 g). The mixture was heated at 150° C.with stirring for 16 hours. The mixture was then cooled and distilled under reduced pressure to give 20 g (62%) of 4-fluoro-2-methylthiopyrimidine as a liquid.

Workup

  1. temperatureThe mixture was then cooled
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-d02271841a334ff1815f17c48731c924
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Linked notes

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