Ammonia → HCID 59875471, compound

HRID 1700099Notes

Reaction equation

HRID 1700099 reaction equation
C([O:4][C@H:5]1[C@@H:9]([O:10]C(=O)C)[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:32]#[N:33])=[N:18][C:19]=3[NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:7][C@@H:6]1[CH2:34][O:35]C(=O)C)(=O)C.N.[H][H]>C(O)C.[Pd]>[NH3:14].[NH2:33][CH2:32][C:17]1[N:16]=[C:15]2[C:20]([N:21]=[CH:22][N:14]2[C@H:8]2[C@H:9]([OH:10])[C@H:5]([OH:4])[C@@H:6]([CH2:34][OH:35])[O:7]2)=[C:19]([NH:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1

Participants

7

Reactant 3

HCID 222Ammonia2×HCID 69970982HCID 69970982, compoundHCID 178418361HCID 178418361, compound2×

Product 2

HCID 222AmmoniaHCID 59875471HCID 59875471, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×

Procedure

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[2-cyano-6-(phenethylamino)-9H-purin-9-yl]tetrahydro-3-furanyl acetate (1.0 g, 1.91 mmol) (Preparation 11) in ethanol (40 ml) saturated with ammonia gas was treated with 5% w/w palladium on charcoal (0.50 g), pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 18 hours. TLC analysis showed that some starting material still remained and therefore further 5% w/w palladium on charcoal (0.25 g) and ethanol (20 ml) saturated with ammonia were added and the mixture was again pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 18 hours. The mixture was filtered through a pad of Arbocel (trade mark) and the filtrate was evaporated under reduced pressure. The residue was azeotroped from dichloromethane, then purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) to afford the title compound as a white solid (340 mg).

Workup

  1. stirringstirred at room temperature for 18 hours
  2. filtrationThe mixture was filtered through a pad of Arbocel (trade mark)
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was azeotroped from dichloromethane
  5. custompurified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-620baf8a24e940e9872aee721c13434b
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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