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Acetonitrile → Toluene-4-sulfonic acid 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

HRID 75643
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인쇄 미리보기

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HRID 75643 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[N:14]([CH3:21])[C:15](=[O:20])[C:16]([CH3:19])=[C:17]([OH:18])[C:12]=3[C:11](=[O:22])[N:10]([CH:23]3[CH2:25][CH2:24]3)[C:9]2=[O:26])=[CH:4][CH:3]=1.C(#N)C.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[N:14]([CH3:21])[C:15](=[O:20])[C:16]([CH3:19])=[C:17]([O:18][S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:12]=3[C:11](=[O:22])[N:10]([CH:23]3[CH2:24][CH2:25]3)[C:9]2=[O:26])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 73974-Toluenesulfonyl chlorideHCID 597170641-(4-bromo-phenyl)-3-cyclopropyl-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

생성물 1

HCID 59717126Toluene-4-sulfonic acid 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester수율 74.3%

시약·촉매·용매 1

HCID 8471
Triethylamine
용매

실험 절차

To 1-(4-bromo-phenyl)-3-cyclopropyl-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 38 (400 mg) obtained in Step 5 was added acetonitrile (8.0 ml), tosyl chloride 11 (458 mg) and triethylamine (0.34 ml) were added under a nitrogen atmosphere, and the mixture was stirred under reflux for 30 hrs. After allowing to cool to room temperature, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (chloroform:acetone=25:1→20:1) to give toluene-4-sulfonic acid 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 39 (407 mg, yield 74%) as ocher crystals.

후처리

  1. additionwere added under a nitrogen atmosphere
  2. temperatureunder reflux for 30 hrs
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (chloroform:acetone=25:1→20:1)

출처 및 근거

ORD 기록
ord-90bcaffae6904cc6a8b3605fb5dc382c
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835443B2

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