Ammonia → 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile

HRID 2268409Notes

Reaction equation

HRID 2268409 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[CH2:50][O:51][CH3:52])(=O)C1C=CC=CC=1.N>CO>[OH:15][C@@H:14]1[C@H:10]([OH:9])[C@@H:11]([CH2:50][O:51][CH3:52])[O:12][C@H:13]1[N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=2[NH:33][CH2:34][CH:35]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59975289(2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

Product 1

HCID 599753059-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrileYield 46.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (preparation 11) (6.75 g, 9.72 mmol) in methanol (300 ml) saturated with ammonia gas was stirred at room temperature for 72 hr. The solvent was removed under reduced pressure, the residue dissolved in dichloromethane and the solvent removed under reduced pressure (repeated). The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2) gradually changing to dichloromethane:methanol (96:4). The residue was triturated with diethyl ether, filtered, washed with diethyl ether and dried to afford the title compound as a solid (2.20 g). MS: 487(MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. customthe solvent removed under reduced pressure (repeated)
  4. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2)
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-dff8ace13ee14e76a0284c4be3f7b7da
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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