Ammonia → (2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 1293027Notes

Reaction equation

HRID 1293027 reaction equation
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=3[NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:12][C@@H:11]1[C:50]([NH:52][CH2:53][CH3:54])=[O:51])(=O)C1C=CC=CC=1.N>[Pd].C(O)C>[NH2:49][CH2:48][C:27]1[N:26]=[C:25]2[C:30]([N:31]=[CH:32][N:24]2[C@@H:13]2[O:12][C@H:11]([C:50]([NH:52][CH2:53][CH3:54])=[O:51])[C@@H:10]([OH:9])[C@H:14]2[OH:15])=[C:29]([NH:33][CH2:34][CH:35]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:28]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58904391(2S,3S,4R,5R)-4-(Benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate

Product 1

HCID 59909598(2S,3S,4R,5R)-5-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamideYield 85.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (400 mg) was added to a solution of (2S,3S,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (Preparation 7) (2.0 g, 2.70 mmol) in a saturated solution of ammonia in ethanol (40 ml). The reaction mixture was stirred under an atmosphere of hydrogen (414 kPa, 60 psi) for 16 hours at room temperature. The suspension was filtered through Arbocel (Trade Mark) and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing to (90:10:1 by volume). This gave the title compound as a solid (1.2 g).

Workup

  1. filtrationThe suspension was filtered through Arbocel (Trade Mark)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing to (90:10:1 by volume)

Sources & evidence

ORD record
ord-beafb2f072c542cba363e2ed1d3bafbf
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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