Methyl iodide → 3-Methyl-1-(2-methylpropyl)-6-(phenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1611019Notes

Reaction equation

HRID 1611019 reaction equation
[O-]CC.[Na+].[C:5]([NH:8][C:9](=[O:32])[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11]1[S:12][C:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:14][C:15]=1[C:16](OCC)=[O:17])(=O)C.IC>C(O)C>[CH3:5][N:8]1[C:16](=[O:17])[C:15]2[CH:14]=[C:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[S:12][C:11]=2[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:9]1=[O:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 22257969HCID 22257969, compound

Product 1

HCID 222579683-Methyl-1-(2-methylpropyl)-6-(phenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 71.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (1.96 g) was added to a solution of N′-acetyl-N-(2-methylpropyl)-N-[3-ethoxycarbonyl-5-(phenylmethyl)-2-thienyl]urea (2.90 g) in ethanol (40 ml) under nitrogen. The mixture was stirred for 20 hours then iodomethane (1.80 ml) was added. The mixture was heated to reflux for 3 hours and then allowed to cool to room temperature and evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate twice. The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography eluting with diethyl ether:isohexane (1:1) to give an oil which was recrystallised from diethyl ether/isohexane to give the title compound (1.70 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customevaporated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate twice
  6. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography
  10. washeluting with diethyl ether:isohexane (1:1)
  11. customto give an oil which
  12. customwas recrystallised from diethyl ether/isohexane

Sources & evidence

ORD record
ord-a33a124a35bb49bfbc87e2656c7d698d
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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