(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate → 9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-(phenethylamino)-9H-purine-2-carbonitrile

HRID 2268432Notes

Reaction equation

HRID 2268432 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:42]#[N:43])=[N:28][C:29]=3[NH:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:12][C@@H:11]1[CH2:44][O:45][CH3:46])(=O)C1C=CC=CC=1>N>[OH:15][C@@H:14]1[C@H:10]([OH:9])[C@@H:11]([CH2:44][O:45][CH3:46])[O:12][C@H:13]1[N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][C:27]([C:42]#[N:43])=[N:28][C:29]=2[NH:33][CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 1

HCID 59975283(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate

Product 1

HCID 599752979-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-(phenethylamino)-9H-purine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent2×

Procedure

(2R,3R,4R,5R)-4-(Benzoyloxy)-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]-2-(methoxymethyl)tetrahydro-3-furanyl benzoate (8.0 g, 19.5 mmol) (preparation 46) was dissolved in a saturated ethanolic solution of ammonia (300 ml). The solution was allowed to stand at room temperature for 24 hr, then re-saturated with ammonia gas and allowed to stand for a further 48 hr. The solvent was then removed under reduced pressure and dichloromethane added to the residue. The dichloromethane was then removed under reduced pressure and more dichloromethane (50 ml) added. The insoluble material was filtered off and dried. This was found to be the title compound (3.1 g) which was a solid.

Workup

  1. waitto stand for a further 48 hr
  2. customThe solvent was then removed under reduced pressure and dichloromethane
  3. additionadded to the residue
  4. customThe dichloromethane was then removed under reduced pressure and more dichloromethane (50 ml)
  5. additionadded
  6. filtrationThe insoluble material was filtered off
  7. customdried

Sources & evidence

ORD record
ord-075fffd2423d4a22a278dc5973ee89f8
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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