Ammonia → (2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268433ノート

反応式

HRID 2268433 の反応式
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4][C@H:3]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([C:29]#[N:30])=[N:15][C:16]=2[NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N.[H][H]>C(O)C.[Pd]>[NH2:30][CH2:29][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@H:3]2[C@H:2]([OH:1])[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4]2)=[C:16]([NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:15]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 599752979-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-(phenethylamino)-9H-purine-2-carbonitrileHCID 178418361HCID 178418361、化合物

生成物 1

HCID 59975306(2R,3R,4S,5R)-2-[2-(aminomethyl)-6-(phenethylamino)-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol収率 58%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-(phenethylamino)-9H-purine-2-carbonitrile (2.9 g, 7.07 mmol) (preparation 47) in ethanol (300 ml), saturated with ammonia gas, was treated with 5% palladium on charcoal (1.0 g), pressurised to 1034 kPa (150 psi) with hydrogen gas in a sealed vessel and stirred at room temperature for 48 hr. The reaction mixture was filtered through Arbocel (trade mark) and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane and the solvent removed under reduced pressure to give a product that was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (92:8:0.4) to give the title compound (1.7 g) as a foam. MS: 416 (MH+)

後処理

  1. filtrationThe reaction mixture was filtered through Arbocel (trade mark)
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customthe solvent removed under reduced pressure
  5. customto give a product that
  6. customwas purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (92:8:0.4)

出典と根拠

ORDレコード
ord-87475b9eba264848b5866cc55928e5e2
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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