Reaction #895

Reaction equation

sodium thiomethoxide

4,6-dichloro-2-(phenylmethoxy)pyrimidine

→

4-chloro-6-methylthio-2-(phenylmethoxy)pyrimidine

Solvents

THF

Conditions

Workup

1. 1
   Otherto react for 2 hours
2. 2
   Otherthe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
3. 3
   WashThe organic layer was washed with aqueous saturated sodium chloride
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified on a silica gel column

Procedure

Aqueous sodium thiomethoxide (15%, 2.75 g, 0.0059×1.0 mol) was added dropwise in 4,6-dichloro-2-(phenylmethoxy)pyrimidine (Compound No. II-26) (1.5 g, 0.0059 mol) dissolved in THF at room temperature. After allowed to react for 2 hours, the reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, then purified on a silica gel column to obtain 4-chloro-6-methylthio-2-(phenylmethoxy)pyrimidine (Compound No. II-15) as an intermediate.

Source