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 75631ノート

反応式

HRID 75631 の反応式
[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

参加物

5

反応物 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

生成物 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 ester収率 82.4%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1857ba0daa8348218256f133e7473108
出典データセット
uspto-grants-2014_09
特許番号
US08835443B2

反応ノート

読み込み中…