Hydrochloric Acid → 7-[4-(4-Chlorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291272

반응식

HRID 1291272 반응식
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:24][CH3:25])[N:20]=[C:21]([O:22]C)[C:16]=4[C:15]([CH3:26])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.S(C1C(C)=CC(O)=C(C(C)(C)C)C=1)C1C(C)=CC(O)=C(C(C)(C)C)C=1.Cl.O>O1CCOCC1>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][N:13]3[C:17]4[N:18]=[C:19]([S:24][CH3:25])[NH:20][C:21](=[O:22])[C:16]=4[C:15]([CH3:26])=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 962WaterHCID 7308SantonoxHCID 189189827-[4-(4-Chlorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 1356675827-[4-(4-Chlorobenzoyl)benzyl]-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one수율 48%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
105 °C

실험 절차

Under argon gas, 7-[4-(4-chlorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (0.671 g) was dissolved in dioxane (8 ml) followed by addition of 4,4'-thiobis(6-t-butyl-m-cresol) (7.2 mg). Then, 0.5N-hydrochloric acid (1.12 ml) was added and the mixture was stirred at 105° C. for 36 hours. Thereafter, 0.5 N-hydrochloric acid (1.12 ml) was added again and the mixture was further stirred at the same temperature as above for 24 hours. To this reaction mixture was added water (30 ml) and the resulting precipitate was collected by filtration and dried. The dried precipitate was purified by flash column chromatography (chloroform) to provide the title compound (0.312 g). 1H-NMR (DMSO-d6) 8: 2.24(3H,s), 2.51(3H,d,J=l.OHz), 5.33(2H,s), 6.83(1H,d,J=l.OHz), 7.43(2H,d,J=8.2Hz), 7.60(2H,d,J=8.6Hz), 7.71(2H,d,J=8.2Hz), 7.73(2H,d,J=8.6Hz), 12.01(1H,s).

후처리

  1. stirringthe mixture was further stirred at the same temperature as above for 24 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried
  4. customThe dried precipitate was purified by flash column chromatography (chloroform)

출처 및 근거

ORD 기록
ord-c5cca570889741218aa4c6604a570c58
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753664

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