6-Chloropurine riboside → HCID 15611205, compound

HRID 845123Notes

Reaction equation

HRID 845123 reaction equation
[C:1]1([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1[N:20]=[C:19](Cl)[C:18]2[N:22]=[CH:23][N:24]([C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[C:17]=2[N:16]=1>>[C:1]1([C:7]2([CH2:13][NH:14][C:19]3[C:18]4[N:22]=[CH:23][N:24]([C:17]=4[N:16]=[CH:15][N:20]=3)[C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 930036-Chloropurine ribosideHCID 205110Cyclohexanemethylamine, 1-phenyl-

Product 1

HCID 15611205HCID 15611205, compoundYield 42.4%

Procedure

(1-Phenylcyclohexyl)methylamine (1.80 g, 8 mmol) as prepared below, and 6-chloropurine riboside (2.36 g, 8 mmol) are reacted as described in Example 1. The solvent is removed under reduced pressure, and the residue dissolved up in CHCl3 and washed with water and dried (MgSO4). The solvent is removed under reduced pressure and the residual white foam is purified on silica gel chromatography eluting with 10% MeOH in CH2Cl2 to give N6-((1-phenylcyclohexyl)methyl)adenosine (1.49 g, 42%) as a white glass m.p. 87°-9° C. Found: C, 62.22; H, 6.96; N, 15.70%. C23H29N5O4 calculated requires: C, 62.87; H, 6.61; N, 15.95%.

Workup

  1. customare reacted
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue dissolved up in CHCl3
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed under reduced pressure
  7. customthe residual white foam is purified on silica gel chromatography
  8. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-652a1ccacd814f8b86b6ed43fbedd285
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

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