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

HRID 897093Notes

Reaction equation

HRID 897093 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>C(O)C>[C: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:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:28]=1)#[N:49]

Participants

4

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 60018592(2S,3S,4R,5R)-5-{2-Cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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) (4.75 g, 6.59 mmol) in ethanol (200 ml) was saturated with ammonia gas and stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5 by volume) gradually changing to dichloromethane:methanol (90:10 by volume) to afford the title compound as a solid (2.80 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5 by volume)

Sources & evidence

ORD record
ord-29ce6b03042f4b29ad7d227f4caa30e1
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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