Ammonia → N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

HRID 2268413Notes

Reaction equation

HRID 2268413 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][C:50]#[N:51])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N.[H][H]>C(O)C.[Ni]>[NH2:51][CH2:50][CH2:49][C:28]1[N:27]=[C:26]2[C:31]([N:32]=[CH:33][N:25]2[C@H:10]2[C@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[C@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]2)=[C:30]([NH:34][CH2:35][CH:36]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:29]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 695341292-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amineYield 56.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}acetonitrile (1.9 g, 2.6 mmol) (preparation 17) in ethanol (40 ml) saturated with ammonia gas was treated with Raney Nickel (400 mg), pressurised to 414 kPa (60 psi) with hydrogen in a sealed vessel and stirred at room temperature for 4 days. 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 pentane and the solvent again removed under reduced pressure to give the title compound as a powder (1.08 g). MS: 733 (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 pentane
  5. customthe solvent again removed under reduced pressure

Sources & evidence

ORD record
ord-728f1ae669a94d60af40060d959ce267
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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