6-Chloropurine riboside → N(6)-cyclohexyl-N(6)-methallyl-adenosine

HRID 328197

Reaction equation

HRID 328197 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]1[OH:13].[CH2:20]([NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:21](=[CH2:23])[CH3:22]>C(O)CCC>[CH:25]1([N:24]([CH2:20][C:21](=[CH2:22])[CH3:23])[C:2]2[C:3]3[N:4]=[CH:5][N:6]([C:7]=3[N:8]=[CH:9][N:10]=2)[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 930036-Chloropurine ribosideHCID 10898899Methallyl-cyclohexylamine

Product 1

HCID 13506439N(6)-cyclohexyl-N(6)-methallyl-adenosineYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4.3 g. 6-chloro-9-(β-D-ribofuranosyl)-purine and 7.6 g. methallyl-cyclohexylamine were heated under reflux for 2 hours in 50 ml. butanol. The reaction mixture was evaporated in a vacuum and the residue obtained was dissolved in 50 ml. ethyl acetate and then extracted twice with 50 ml. amounts of water. The organic phase was dried, again evaporated and the residue recrystallized from methanol. 2.6 g. (43% of theory) N(6)-cyclohexyl-N(6)-methallyl-adenosine were obtained; m.p. 110°- 112° C.

Workup

  1. temperatureunder reflux for 2 hours in 50 ml
  2. customThe reaction mixture was evaporated in a vacuum
  3. customthe residue obtained
  4. dissolutionwas dissolved in 50 ml
  5. extractionethyl acetate and then extracted twice with 50 ml
  6. customThe organic phase was dried
  7. customagain evaporated
  8. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-fe48b4d6cc5c4f06b118f1810568dc85
Source dataset
uspto-grants-1977_04
Patent number
US04016262

Linked notes

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