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

HRID 1031070

反応式

HRID 1031070 の反応式
[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]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10376467HCID 10376467、化合物HCID 145239709-Hydroxy-6-phthalimidopurine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-404cbf1e8bf24a3e8bc3b8b66d880dab
出典データセット
uspto-grants-1992_04
特許番号
US05108994

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