HCID 60018586, compound → (2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(3-methylphenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol

HRID 1293055Notes

Reaction equation

HRID 1293055 reaction equation
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:40]#[N:41])=[N:18][C:19]=3[NH:23][CH2:24][CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[O:7][C@@H:6]1[CH2:42][O:43]C(=O)C)(=O)C>N.C(O)C.[Pd]>[NH2:41][CH2:40][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@H:8]2[C@H:9]([OH:10])[C@H:5]([OH:4])[C@@H:6]([CH2:42][OH:43])[O:7]2)=[C:19]([NH:23][CH2:24][CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[N:18]=1

Participants

5

Reactant 1

HCID 60018586HCID 60018586, compound

Product 1

HCID 60018578(2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(3-methylphenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiolYield 50.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-{[2,2-bis(3-methylphenyl)ethyl]amino}-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate (620 mg, 1 mmol) (Preparation 66) was dissolved in a saturated solution of 0.88 concentrated aqueous ammonia in ethanol (20 ml). The solution was then stirred under an atmosphere of hydrogen gas (414 kPa, 60 psi) at room temperature for 64 hours in the presence of 10% Palladium on carbon (120 mg). The reaction mixture was then filtered through Arbocel (Trade Mark) and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:(90:10 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (80:20:2 by volume). The solvent was removed under reduced pressure to give the title compound (253 mg) as a foam.

Workup

  1. filtrationThe reaction mixture was then filtered through Arbocel (Trade Mark)
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:(90:10 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0dca4e4fce8841dca78bf78ea2ff5aa7
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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