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

HRID 1291272

反応式

HRID 1291272 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 962WaterHCID 7308SantonoxHCID 189189827-[4-(4-Chlorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c5cca570889741218aa4c6604a570c58
出典データセット
uspto-grants-1998_05
特許番号
US05753664

関連ノート

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