Ammonia → HCID 59875475, compound

HRID 1700102Notes

Reaction equation

HRID 1700102 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:31]#[N:32])=[N:14][C:15]=2[NH:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.N.[H][H]>C(O)C.[Pd]>[NH3:10].[NH2:32][CH2:31][C:13]1[N:12]=[C:11]2[C:16]([N:17]=[CH:18][N:10]2[C@H:3]2[C@H:2]([OH:1])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4]2)=[C:15]([NH:19][CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)[N:14]=1

Participants

7

Reactant 3

HCID 222Ammonia2×HCID 59875466HCID 59875466, compoundHCID 178418361HCID 178418361, compound2×

Product 2

HCID 222AmmoniaHCID 59875475HCID 59875475, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×

Procedure

A solution of 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(1-naphthylmethyl)amino]-9H-purine-2-carbonitrile (0.75 g, 1.74 mmol) (Preparation 14) in ethanol (30 ml) was saturated with ammonia gas, 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 42 hours. TLC analysis indicated that some starting material still remained and therefore further 5% w/w palladium on charcoal (0.30 g) and ethanol (10 ml) saturated with ammonia gas were added. The mixture was re-pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 24 hours. The mixture was filtered through a pad of Arbocel (trade mark) and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:0.88 ammonia (90:10:0.5 by volume) gradually changing to dichloromethane:methanol:0.88 ammonia (85:15:0.75 by volume) to afford the title compound (0.18 g).

Workup

  1. stirringstirred at room temperature for 24 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 purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Sources & evidence

ORD record
ord-5e70464296594c6fb3707ff3d3bdea3c
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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