Ammonium formate → 6-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-(4-piperidinyl)-9H-purine-2-carboxamide

HRID 10454Notes

Reaction equation

HRID 10454 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:25]=[C:24]3[C:20]([N:21]=[CH:22][N:23]3[C@H:26]3[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[O:27]3)=[C:19]([NH:38][CH2:39][CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:18]=2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[C:41]1([CH:40]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH2:39][NH:38][C:19]2[N:18]=[C:17]([C:15]([NH:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[O:16])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@H:26]2[C@H:30]([OH:31])[C@H:29]([OH:32])[C@@H:28]([C:33]([NH:35][CH2:36][CH3:37])=[O:34])[O:27]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 60091679N-(1-Benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide

Product 1

HCID 600916826-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-(4-piperidinyl)-9H-purine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(1-benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 33) (1.03 g, 1.47 mmol), palladium (II) hydroxide (0.9 g) and ammonium formate (0.46 g, 7.3 mmol) in ethanol (10 ml) was heated under reflux for 3 hours. The catalyst was removed by filtration through Arbocel (trade mark), solvent removed by evaporation under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane: methanol:concentrated aqueous ammonia (80:20:2, by volume). After evaporation of appropriate fractions the target compound was obtained as a white solid, (0.6 g, 67%).

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe catalyst was removed by filtration through Arbocel (trade mark), solvent
  3. customremoved by evaporation under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  5. customAfter evaporation of appropriate fractions the target compound
  6. customwas obtained as a white solid, (0.6 g, 67%)

Sources & evidence

ORD record
ord-9f53c36c189340a68a9f5c76b3e8b421
Source dataset
uspto-grants-2006_08
Patent number
US07094769B2

Reaction notes

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