Ammonia → (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol

HRID 1293028Notes

Reaction equation

HRID 1293028 reaction equation
N.C([O:5][C@H:6]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][C:18]([C:39]#[N:40])=[N:19][C:20]=3[NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:8][C@@H:7]1[CH2:41][O:42]C(=O)C)(=O)C>C(O)C.[Pd]>[NH2:40][CH2:39][C:18]1[N:17]=[C:16]2[C:21]([N:22]=[CH:23][N:15]2[C@H:9]2[C@H:10]([OH:11])[C@H:6]([OH:5])[C@@H:7]([CH2:41][OH:42])[O:8]2)=[C:20]([NH:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:19]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 60018587(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl) amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate

Product 1

HCID 60018582(2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiolYield 37.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ammonia gas was passed through an ice cold solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-{2-cyano-6-[(9H-fluoren-9-ylmethyl)amino]-9H-purin-9-yl}tetrahydro-3-furanyl acetate (1.2 g, 2 mmol) (Preparation 71) in ethanol (40 ml) until the solution was saturated. 10% Palladium on carbon (120 mg) was added and the reaction mixture was stirred under an atmosphere of hydrogen gas (413.7 kPa, 60 psi) at room temperature for 40 hours. The suspension was filtered through Arbocel (Trade Mark) and the solvent was removed from the filtrate under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (94:6:0.5 by volume). The solvent was removed under reduced pressure to give the title compound (358 mg) as a foam.

Workup

  1. filtrationThe suspension was filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (96:4:0.4 by volume) increasing in polarity to dichloromethane
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f292a6f2b0444927896c5e3d86817f07
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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