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

HRID 269856

Reaction equation

HRID 269856 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-2b0484fd0ed1495ea3cc2857c7e24776
Source dataset
uspto-grants-2008_11
Patent number
US07449472B2

Linked notes

Loading…