Potassium Cyanide → 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

HRID 2268412ノート

反応式

HRID 2268412 の反応式
CS(O[CH2:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[C@H:19]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:18]([CH2:37][O:38][CH3:39])[O:17]2)=[C:9]([NH:40][CH2:41][CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:8]=1)(=O)=O.[C-:55]#[N:56].[K+]>CN(C)C=O>[Si:22]([O:21][C@@H:20]1[C@H:19]([O:29][Si:30]([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:31])[CH3:32])[C@@H:18]([CH2:37][O:38][CH3:39])[O:17][C@H:16]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:7]([CH2:6][C:55]#[N:56])=[N:8][C:9]=2[NH:40][CH2:41][CH:42]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:25]([CH3:26])([CH3:28])[CH3:27])([CH3:23])[CH3:24]

参加物

4

反応物 2

HCID 9032Potassium CyanideHCID 86757641{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}methyl methanesulfonate

生成物 1

HCID 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}acetonitrile収率 80.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
67.5 °C

実験手順

A stirred solution of {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}methyl methanesulfonate (3.0 g, 3.76 mmol) (preparation 16) in anhydrous N,N-dimethylformamide (20 ml) was treated with potassium cyanide (0.37 g, 5.69 mmol) and heated to 65-70° C. for 3 hr. The mixture was cooled to room temperature and partitioned between diethyl ether and water. The organic phase was separated and the aqueous phase extracted again with diethyl ether. The combined organic solutions were then washed with brine, dried with anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent system of diethyl ether:pentane (1:1) to afford the title compound as a foam (2.2 g). MS: 751 (MNa+).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned between diethyl ether and water
  3. customThe organic phase was separated
  4. extractionthe aqueous phase extracted again with diethyl ether
  5. washThe combined organic solutions were then washed with brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel eluting with a solvent system of diethyl ether:pentane (1:1)

出典と根拠

ORDレコード
ord-c90b054166d543e6847807decd8fb457
出典データセット
uspto-grants-2001_12
特許番号
US06326359B1

反応ノート

読み込み中…