Phenethylamine → 6-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-(2-phenylethyl)-9H-purine-2-carboxamide

HRID 1168276Notes

Reaction equation

HRID 1168276 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([C:45]([O:47]C)=O)=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=CC=CC=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.[C:49]1([CH2:55][CH2:56][NH2:57])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>>[C:33]1([CH:32]([C:39]2[CH:8]=[CH:9][CH:5]=[CH:6][CH:44]=2)[CH2:31][NH:30][C:26]2[N:25]=[C:24]([C:45]([NH:57][CH2:56][CH2:55][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[O:47])[N:23]=[C:22]3[C:27]=2[N:28]=[CH:29][N:21]3[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=3)[O:7]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 59094502Methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetraazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

Product 1

HCID 590945176-[(2,2-Diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-N-(2-phenylethyl)-9H-purine-2-carboxamideYield 100.9%

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 9-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 30) (100 mg, 0.15 mmol) and 2-phenylethylamine (0.2 ml, 1.58 mmol) were heated together under a nitrogen atmosphere at 130° C. for three hours. The mixture was allowed to cool to room temperature and was then purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate gradually changing to ethyl acetate:methanol (95:5 by volume). Product containing fractions were evaporated and the resulting solid was triturated with ether, filtered and dried to afford the title compound as a white powder (50 mg).

Workup

  1. temperatureto cool to room temperature
  2. customwas then purified by column chromatography on silica gel eluting with a gradient system of ethyl acetate
  3. additionProduct containing fractions
  4. customwere evaporated
  5. customthe resulting solid was triturated with ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-8ca08dbf8cae4970a3e4e85ab6a927b9
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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