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

HRID 1611019노트

반응식

HRID 1611019 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a33a124a35bb49bfbc87e2656c7d698d
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984644B2

반응 노트

불러오는 중…