Ammonia → N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

HRID 2268413ノート

反応式

HRID 2268413 の反応式
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][C:50]#[N:51])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N.[H][H]>C(O)C.[Ni]>[NH2:51][CH2:50][CH2:49][C:28]1[N:27]=[C:26]2[C:31]([N:32]=[CH:33][N:25]2[C@H:10]2[C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[C@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]2)=[C:30]([NH:34][CH2:35][CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:29]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 695341292-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine収率 56.7%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

A solution of 2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile (1.9 g, 2.6 mmol) (preparation 17) in ethanol (40 ml) saturated with ammonia gas was treated with Raney Nickel (400 mg), pressurised to 414 kPa (60 psi) with hydrogen in a sealed vessel and stirred at room temperature for 4 days. The mixture was then filtered through Arbocel (trade mark) and the residue washed with ethanol. The solvent was removed under reduced pressure from the filtrate, the residue dissolved in pentane and the solvent again removed under reduced pressure to give the title compound as a powder (1.08 g). MS: 733 (MH+).

後処理

  1. filtrationThe mixture was then filtered through Arbocel (trade mark)
  2. washthe residue washed with ethanol
  3. customThe solvent was removed under reduced pressure from the filtrate
  4. dissolutionthe residue dissolved in pentane
  5. customthe solvent again removed under reduced pressure

出典と根拠

ORDレコード
ord-728f1ae669a94d60af40060d959ce267
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

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