2-Chloroadenosine → 2-(6-Amino-2-{2-[4-(2-cyclohexyl-ethyl)-phenyl]-ethylamino}-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

HRID 1087014Notes

Reaction equation

HRID 1087014 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH:21]1([CH2:27][CH2:28][C:29]2[CH:37]=[CH:36][C:32]([CH2:33][CH2:34][NH2:35])=[CH:31][CH:30]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH2:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:33][CH2:34][NH:35][C:2]2[N:3]=[C:4]([NH2:20])[C:5]3[N:6]=[CH:7][N:8]([C:18]=3[N:19]=2)[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 89742-ChloroadenosineHCID 150366412-[4-(2-Cyclohexyl-ethyl)-phenyl]-ethylamine

Product 1

HCID 150366422-(6-Amino-2-{2-[4-(2-cyclohexyl-ethyl)-phenyl]-ethylamino}-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Procedure

Reaction of 2-chloroadenosine with p-(2-cyclohexylethyl)-phenethylamine as described in Example 14 gives 2-[2-(p-2-cyclohexylethyl-phenyl)-ethylamino]-adenosine, [alpha]D25 =-25.6° in DMSO, m.p. 154°-160°.

Sources & evidence

ORD record
ord-59f2d1aecaf5447093d2c69d9f2dc7b0
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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