Acetonitrile → Toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

HRID 75631노트

반응식

HRID 75631 반응식
[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([OH:17])=[CH:12][C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[C:5]2=[O:27])[CH2:3][CH2:2]1.C(#N)C.[S:31](Cl)([C:34]1[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=1)(=[O:33])=[O:32]>C(N(CC)CC)C>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([O:17][S:31]([C:34]4[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=4)(=[O:33])=[O:32])=[CH:12][C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)[C:5]2=[O:27])[CH2:2][CH2:3]1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 73974-Toluenesulfonyl chlorideHCID 597172003-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

생성물 1

HCID 59717031Toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester수율 82.4%

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
110 °C

실험 절차

To 3-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 10 (18 g) obtained in Step 5 were added acetonitrile (180 ml), tosyl chloride 11 (11 g) and triethylamine (8 ml), and the mixture was stirred with heating under reflux at 110° C. for 1 hr. The reaction mixture was concentrated under reduced pressure. Water (100 ml) was added to the residue and the mixture was extracted with chloroform (800 ml). The organic layer was washed with brine (50 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from chloroform:diethyl ether=1:5 to give toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 12 (21 g, 82%) as a white solid.

후처리

  1. temperaturewith heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater (100 ml) was added to the residue
  4. extractionthe mixture was extracted with chloroform (800 ml)
  5. washThe organic layer was washed with brine (50 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from chloroform

출처 및 근거

ORD 기록
ord-1857ba0daa8348218256f133e7473108
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835443B2

반응 노트

불러오는 중…