Dimethylformamide → 6-(3-H-Benzimidazol-5-yl)methylsulfanyl-9-beta-D-ribofuranosyl-9H-purine

HRID 900059

반응식

HRID 900059 반응식
[I-].[C:2]([CH2:4][P+](C)(C)C)#[N:3].[CH:9]1[NH:15][C:14]2[N:16]([C@@H:19]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@H:20]3[OH:27])[CH:17]=[N:18][C:13]=2[C:11](=[S:12])[N:10]=1.CC[N:30]([CH:34](C)C)[CH:31]([CH3:33])C.CN(C=O)C.[C:42](#N)[CH2:43][CH3:44]>O>[N:30]1[C:31]2[CH:33]=[CH:42][C:43]([CH2:44][S:12][C:11]3[N:10]=[CH:9][N:15]=[C:14]4[C:13]=3[N:18]=[CH:17][N:16]4[C@@H:19]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:21]([OH:26])[C@H:20]3[OH:27])=[CH:4][C:2]=2[NH:3][CH:34]=1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 7854PropionitrileHCID 81531DiisopropylethylamineHCID 6761666-ThioinosineHCID 10514344(Cyanomethyl)trimethylphosphanium iodide

생성물 1

HCID 1317268196-(3-H-Benzimidazol-5-yl)methylsulfanyl-9-beta-D-ribofuranosyl-9H-purine수율 65%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

(Cyanomethyl)trimethyl-phosphonium iodide 36 (299 mg, 1.23 mmol) was added to a mixture of alcohol 35 (200 mg, 1.35 mmol), 6-mercaptopurine riboside (284 mg, 1.00 mmol), and DIPEA (0.25 mL) in propionitrile (3 mL). The mixture was heated at 90° C. and some drops of DMF were added to obtain a clear solution. The mixture was stirred overnight at 90° C., cooled to room temperature and water was added. Upon standing at room temperature, 37 was formed as a pale brown precipitate collected by filtration and dried in vacuo (65% yield). 1H NMR (d6-DMSO): δ 8.83, 8.72 (2×s, 2H), 8.21 (s, 1H), 7.70 (s, 1H), 7.54 (d, 1H, J=8.04 Hz), 7.31 (d, 1H, J=8.04 Hz), 6.01 (d, 1H, J=5.85 Hz), 5.57 (d, 1H, J=5.85 Hz), 5.27 (d, 1H, J=5.11 Hz), 5.16 (m, 1H), 4.81 (s, 2H), 4.62 (m, 1H), 4.19 (m, 2H), 3.99 (m, 1H); 13C NMR (d6-DMSO): δ 162.0, 152.8, 149.5, 144.5, 133.7, 132.6, 125.2, 90.5, 87.6, 75.7, 72.2, 63.0, 33.9; Mp: 196-198° C.; HRMS calc. for C18H19N6O4S m/z=415.1200 (M+H), found 415.1155.

후처리

  1. customto obtain a clear solution
  2. temperaturecooled to room temperature
  3. customUpon standing at room temperature
  4. custom37 was formed as a pale brown precipitate
  5. filtrationcollected by filtration
  6. customdried in vacuo (65% yield)

출처 및 근거

ORD 기록
ord-f787920757a94a75a98ad57d611c7e3f
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358235B2

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