Acetic Acid → 2-methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one

HRID 9768

Reaction equation

HRID 9768 reaction equation
[S:1]=[C:2]1[NH:7][C:6]2[S:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3]1.CI.[C:14](O)(=O)C>[OH-].[Na+]>[CH3:14][S:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 36033932-sulfanyl-3H,4H-thieno(2,3-d)pyrimidin-4-one

Product 1

HCID 38520912-methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-thioxo-2,3-dihydro-1H-thieno[2,3-d]pyrimidin-4-one (25.4 g, 0.138 mol) in 1N aqueous NaOH (600 mL) at room temperature was added methyl iodide (10.3 mL, 1.2 eq). The resulting mixture was stirred vigorously for about 2.5 hours. The reaction mixture was cooled to 0° C. and acetic acid was added (about 80 mL) until about pH=4.5 was reached. A fine precipitate was filtered and dried overnight to afford the title compound as a fine tan powder (24.8 g) (M+=198, M.P.=231.6–235.0° C.).

Workup

  1. filtrationA fine precipitate was filtered
  2. customdried overnight

Sources & evidence

ORD record
ord-53c7f10c5ffc4baebb47a80de51c29b8
Source dataset
uspto-grants-2006_08
Patent number
US07091347B2

Linked notes

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