Sodium methanethiolate → 4-Chloro-6-methylthio-2-(phenylmethoxy)pyrimidine

HRID 799

Reaction equation

HRID 799 reaction equation
[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[CH:10]=[C:9](Cl)[N:8]=[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1>C1COCC1>[Cl:4][C:5]1[CH:10]=[C:9]([S:2][CH3:1])[N:8]=[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 196938984,6-Dichloro-2-(phenylmethoxy)pyrimidine

Product 1

HCID 196938764-Chloro-6-methylthio-2-(phenylmethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customto react for 2 hours
  2. customthe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  3. washThe organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-bbaa547034cb4578bce2648d1c091a1f
Source dataset
uspto-grants-1998_03
Patent number
US05723412

Linked notes

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