6-Chloropurine riboside → HCID 15611199, compound

HRID 845120Notes

Reaction equation

HRID 845120 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:14]1[N:19]=[C:18](Cl)[C:17]2[N:21]=[CH:22][N:23]([C@@H:24]3[O:28][C@H:27]([CH2:29][OH:30])[C@@H:26]([OH:31])[C@H:25]3[OH:32])[C:16]=2[N:15]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][NH:13][C:18]3[C:17]4[N:21]=[CH:22][N:23]([C:16]=4[N:15]=[CH:14][N:19]=3)[C@@H:24]3[O:28][C@H:27]([CH2:29][OH:30])[C@@H:26]([OH:31])[C@H:25]3[OH:32])[CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 930036-Chloropurine ribosideHCID 156111771-[1-(3-Chlorophenyl)cyclobutyl]methanamine

Product 1

HCID 15611199HCID 15611199, compoundYield 82.1%

Procedure

The above amine (1.96 g, 10 mmol) is reacted with 6-chloropurine riboside (2.87 g, 10 mmol) and purified as described in Examples 1 and 7 above. N6-((1-(3-chlorophenyl)cyclobutyl)methyl)adenosine (3.66 g, 82%) as a pale yellow solid foam is obtained m.p. 92°-8° C. Found: C, 56.11; H, 5.33; N, 15.44; Cl, 8.99%. C21H24ClN5O4 calculated requires: C, 56.57; H, 5.39; N, 15.71; Cl, 7.97%.

Workup

  1. custompurified

Sources & evidence

ORD record
ord-056abcda2c064f0f9624c3e2dd04322c
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

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