Ammonia → (2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268340Notes

Reaction equation

HRID 2268340 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4][C@H:3]1[N:11]1[CH:19]=[N:18][C:17]2[C:12]1=[N:13][C:14]([C:35]#[N:36])=[N:15][C:16]=2[NH:20][CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N.[H][H]>C(O)C.[Pd]>[NH2:36][CH2:35][C:14]1[N:13]=[C:12]2[C:17]([N:18]=[CH:19][N:11]2[C@H:3]2[C@H:2]([OH:1])[C@H:6]([OH:7])[C@@H:5]([CH2:8][O:9][CH3:10])[O:4]2)=[C:16]([NH:20][CH2:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:15]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 599753059-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carbonitrile (preparation 12) (2.15 g, 4.42 mmol) in ethanol (120 ml) saturated with ammonia gas was treated with 5% palladium on charcoal (1 g), pressurised to 1034 kPa (150 psi) with hydrogen in a sealed vessel and stirred at room temperature for 24 hr. The mixture was then filtered through Arbocel (trade mark) and the residue washed with ethanol. The solvent was removed under reduced pressure from the filtrate, the residue dissolved in ethanol and the solvent again removed under reduced pressure. A solid precipitated on re-evaporation which was then dissolved in hot ethanol (100 ml) and the solution cooled and filtered. The residue was washed with ethanol then diethyl ether and dried to give the title compound as an off white solid (1.05 g, 48%). The filtrate and washings were combined and the solvent removed under reduced pressure to give a residue which was then triturated with dichloromethane and a few drops of ethanol and filtered to afford a further portion of product (0.45 g). MS: 491 (MH+).

Workup

  1. filtrationThe mixture was then filtered through Arbocel (trade mark)
  2. washthe residue washed with ethanol
  3. customThe solvent was removed under reduced pressure from the filtrate
  4. dissolutionthe residue dissolved in ethanol
  5. customthe solvent again removed under reduced pressure
  6. customA solid precipitated on re-evaporation which
  7. dissolutionwas then dissolved in hot ethanol (100 ml)
  8. temperaturethe solution cooled
  9. filtrationfiltered
  10. washThe residue was washed with ethanol
  11. dry with materialdiethyl ether and dried

Sources & evidence

ORD record
ord-644c6b08613c48bbaaaeaaa884436022
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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