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

HRID 2268433노트

반응식

HRID 2268433 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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+)

후처리

  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)

출처 및 근거

ORD 기록
ord-87475b9eba264848b5866cc55928e5e2
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326359B1

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