Methyl iodide → 2-(Methylthio)-3-propylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1108245Notes

Reaction equation

HRID 1108245 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8]2[S:11][CH:12]=[CH:13][C:7]=2[NH:6][C:5]1=[S:14])[CH2:2][CH3:3].I[CH3:16]>[OH-].[Na+]>[CH3:16][S:14][C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[C:9](=[O:10])[C:8]2[S:11][CH:12]=[CH:13][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 16767826HCID 16767826, compound

Product 1

HCID 211838812-(Methylthio)-3-propylthieno[3,2-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture containing 3.6 g of the title compound of Step A suspended in 70 mL of 10% propanolic sodium hydroxide was added 1.46 mL of iodomethane with stirring. The mixture was stirred at room temperature for 1 h, then cooled to 0° C. and filtered to obtain an off-white solid. The off-white solid was purified by partially dissolving it in methylene chloride, filtering and evaporating the filtrate to obtain 3.13 g of the title compound of Step B as a white solid melting at 136-138° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. filtrationfiltered
  3. customto obtain an off-white solid
  4. customThe off-white solid was purified
  5. dissolutionby partially dissolving it in methylene chloride
  6. filtrationfiltering
  7. customevaporating the filtrate

Sources & evidence

ORD record
ord-dae9942a8c844c04a3586ff166776447
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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