Water → 4-(Methylsulfanyl)thieno[3,2-d]pyrimidine

HRID 32529Notes

Reaction equation

HRID 32529 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[C:6]2[S:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.O>CN(C=O)C>[CH3:1][S:2][C:5]1[C:6]2[S:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 179658614-(Methylsulfanyl)thieno[3,2-d]pyrimidineYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thiomethoxide (9.1 g) was added to a solution of 4-chlorothieno[3,2-d]pyrimidine (WO9849899, example 3A; WO9924440, example 1C) (17.0 g) in DMF (100 mL). After stirring for 90 minutes the mixture was poured into water (400 mL), extracted into EtOAc, washed with water, dried (MgSO4), and the solvent removed. Purification by flash chromatography on silica eluting with DCM:EtOAc (4:1) gave the title compound as a pale yellow solid (16.5 g, 69%);

Workup

  1. extractionextracted into EtOAc
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed
  5. customPurification by flash chromatography on silica eluting with DCM:EtOAc (4:1)

Sources & evidence

ORD record
ord-08effa3202724c31bdb5bcf7475c46f1
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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