Triphenylphosphine → 9-[2-(Diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine

HRID 1031070

반응식

HRID 1031070 반응식
[OH:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].[CH2:22]([O:24][P:25]([CH2:30][S:31][CH2:32][CH2:33]O)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:22]([O:24][P:25]([CH2:30][S:31][CH2:32][CH2:33][O:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O:26][CH2:27][CH3:28])=[O:29])[CH3:23]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10376467HCID 10376467, 화합물HCID 145239709-Hydroxy-6-phthalimidopurine

생성물 1

HCID 198195589-[2-(Diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 9-hydroxy-6-phthalimidopurine (0.5 g, 2.2 mmol). diethyl-2-hydroxyethylthiomethylphosphonate (0.45 g. 2 mmol) and triphenylphosphine (0.52 g, 2 mmol) was dissolved in dry tetrahydrofuran (20 ml) and cooled to 0°-5° C. A solution of diethylazodicarboxylate (0.348 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) was added dropwise with stirring, and after the addition was completed the reaction was stirred at room temperature for 18 hours. The solvent was then removed in vacuo, and the residue was purified by column chromatography on silica using ethyl acetate: methanol (98:2) as eluent to give 9-[2-(diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine (0.45 g 56%) as a white solid after crystallisation from acetone/diethyl ether, m.p. 115°-116° C.; γmax (EtOH) 271mm (s 14020) υmax (KBr) 3100, 3060, 2960, 2900, 1780, 1725, 1650, 1600, 1580, 1453, 1400, 1380, 1360, 1320, 1280, 1240, and 1200 cm-1 ; δH [(CD3)2SO] 1.25 (6H, t, J 7Hz 2 × CH3), 3.0 (2H, d, J 13Hz, PCH2S), 3.1 (2H, t, J 7Hz CH20, 4.0 (4H, m, 2 × CH2), 4.7 (2H, t, J 7Hz, CH2S), 8.1 (4H, m, Ar H), 9.0 (1H, s, 2H), 9.1 (1H, s, 8-H). (Found C, 48.65; H, 4.55; N, 14.23%. C20H22N5O6PS requires C,48.87; H, 4.51; N, 14.25%).

후처리

  1. temperaturecooled to 0°-5° C
  2. additionafter the addition
  3. stirringwas stirred at room temperature for 18 hours
  4. customThe solvent was then removed in vacuo
  5. customthe residue was purified by column chromatography on silica

출처 및 근거

ORD 기록
ord-404cbf1e8bf24a3e8bc3b8b66d880dab
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05108994

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