6-chloro-2-methyl-9-(beta-D-ribofuranosyl)-9H-purine → HCID 178433181, compound

HRID 1086803Notes

Reaction equation

HRID 1086803 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]1[OH:14].Cl.[NH2:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([OH:29])[CH2:25][CH2:24]1>C(O)(C)C>[OH:29][C@H:26]1[CH2:27][CH2:28][C@H:23]([NH:22][C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[C:9]([CH3:11])[N:10]=2)[C@@H:12]2[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]2[OH:14])[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 542785016-chloro-2-methyl-9-(beta-D-ribofuranosyl)-9H-purineHCID 178479278HCID 178479278, compound

Product 1

HCID 178433181HCID 178433181, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-chloro-2-methyl-9-(β-D-ribofuranosyl)-9H-purine (902 mg), trans-4-aminocyclohexanol hydrochloride (1.14 g) and DEA (1.94 g) in isopropanol (50 ml) was heated at reflux with stirring under nitrogen for 17 h. The resulting cooled reaction mixture was adsorbed onto silica (Merck 9385) and purified by column chromatography on silica (Merck 9385) eluting with System B (10:1 then 8:1) to give the title compound (0.9 g) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe resulting cooled
  4. customreaction mixture
  5. custompurified by column chromatography on silica (Merck 9385)
  6. washeluting with System B (10:1

Sources & evidence

ORD record
ord-eee0310c533c4584987382826d592722
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

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