Ethanol → 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one

HRID 1714761

반응식

HRID 1714761 반응식
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S-:14].[K+].NC1SC(C)=C(C)C=1C(OCC)=O.Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1.C(O)C>C(Cl)(Cl)Cl>[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S:14][CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1

참가 물질

6

반응물 4

HCID 702EthanolHCID 78536Ethyl 2-amino-4,5-dimethyl3-thenoateHCID 30355894-(Chloropropyl)-1-(2-quinolyl)piperazineHCID 23701453Potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate

생성물 1

HCID 111908233-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one수율 50%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 80 mg of potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate, which was prepared from ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate; 104 mg of 2-[4-(3-chloropropyl)piperazin-1-yl]quinoline as prepared in the Step 1-1-B; and 5 ml of ethanol, was heated under reflux for 4.5 hours. After cooling off the reaction mixture, chloroform was added, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=100: 1) to provide 72 mg (50%) of 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one.

후처리

  1. temperatureunder reflux for 4.5 hours
  2. additionwas added
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified on silica gel column chromatography (chloroform:methanol=100: 1)

출처 및 근거

ORD 기록
ord-cc6cd19d999744c9a3292ecfedcae500
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799775B2

연결된 노트

불러오는 중…