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

HRID 567896ノート

反応式

HRID 567896 の反応式
[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]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2723922Sodium ethoxideHCID 22257969HCID 22257969、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f2288bee44884a0390ab4abaa5efffd8
出典データセット
uspto-grants-2001_01
特許番号
US06180635B2

反応ノート

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