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

HRID 1384849Notes

Reaction equation

HRID 1384849 reaction equation
[H-].[Na+].[CH2:3]([N:6]1[C:11](=[O:12])[C:10]2[S:13][CH:14]=[CH:15][C:9]=2[NH:8][C:7]1=[S:16])[CH2:4][CH3:5].[CH3:17]I>O1CCCC1>[CH3:17][S:16][C:7]1[N:6]([CH2:3][CH2:4][CH3:5])[C:11](=[O:12])[C:10]2[S:13][CH:14]=[CH:15][C:9]=2[N:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16767826HCID 16767826, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a sulfonation flask, 0.84 g (0.021 mol) of a ˜60% sodium hydride dispersion is added to 20 ml of absolute tetrahydrofuran, and then 4.8 g (0.021 mol) of 3-propyl-2-thioxo-2,3-dihydro-1H-thieno-[3.2-d]pyrimidin-4-one, dissolved in 80 ml of tetrahydrofuran, are added dropwise such that the internal temperature remains constant at about 25° C. The mixture is stirred for 1 hour at room temperature and then 4.3 g (0.03 mol) of methyl iodide are added all at once. The mixture is refluxed for 4 hours and then the tetrahydrofuran is removed in a water-jet vacuum. The residue is taken up in ethyl acetate and the organic phase is extracted three times with water. The organic phase is dried over sodium sulfate and the solvent is removed in the water-jet vacuum, giving the crude product which is purified by column chromatography over silica gel (eluant: ethyl acetate/hexane 1:3). 2-Methylsulfanyl-3-propyl-3H-thieno[3.2-d]pyrimidin-4-one is obtained in virtually quantitative yield and having a melting point of 142-144° C.

Workup

  1. additionare added dropwise such that the internal temperature
  2. customremains constant at about 25° C
  3. temperatureThe mixture is refluxed for 4 hours
  4. customthe tetrahydrofuran is removed in a water-jet vacuum
  5. extractionthe organic phase is extracted three times with water
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customthe solvent is removed in the water-jet vacuum
  8. customgiving the crude product which
  9. customis purified by column chromatography over silica gel (eluant: ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-1b1b60d263ee44d1a7c4405a85bccdf9
Source dataset
uspto-grants-2001_07
Patent number
US06262058B1

Reaction notes

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