2-Chloroadenosine → 2-((2-(1-Cyclohexen-1-yl)ethyl)amino)adenosine

HRID 1087012Notes

Reaction equation

HRID 1087012 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].[C:21]1([CH2:27][CH2:28][NH2:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1>>[C:21]1([CH2:27][CH2:28][NH:29][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])[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]=1

Participants

3

Reactant 2

HCID 89742-ChloroadenosineHCID 769382-(1-Cyclohexenyl)ethylamine

Product 1

HCID 1301982-((2-(1-Cyclohexen-1-yl)ethyl)amino)adenosine

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloroadenosine (0.30 g) and 2-(1-cyclohexenyl)-ethylamine (0.63 g) is stirred under nitrogen for 6 hours at 140° C. The solution is concentrated to dryness at reduced pressure; the residue is dissolved in ethanol, treated with propylene oxide (2 ml) and stirred at room temperature for 16 hours. The mixture is concentrated to dryness at reduced pressure and flash chromatographed through a 25×150 mm column of silica gel using methylene chloride and methanol saturated with ammonia (9:1) as eluent. Fractions containing the desired product are combined, concentrated to dryness at reduced pressure; the residue is redissolved in hot ethanol, the solution is decolorized with charcoal and then concentrated to dryness. The residual solid is triturated with ethanol (2 ml) and collected to afford 2-[2-(1-cyclohexenyl)-ethylamino]adenosine, m.p. 135°-38°.

Workup

  1. concentrationThe solution is concentrated to dryness at reduced pressure
  2. dissolutionthe residue is dissolved in ethanol
  3. additiontreated with propylene oxide (2 ml)
  4. stirringstirred at room temperature for 16 hours
  5. concentrationThe mixture is concentrated to dryness at reduced pressure and flash
  6. customchromatographed through a 25×150 mm column of silica gel
  7. additionFractions containing the desired product
  8. concentrationconcentrated to dryness at reduced pressure
  9. dissolutionthe residue is redissolved in hot ethanol
  10. concentrationconcentrated to dryness
  11. customThe residual solid is triturated with ethanol (2 ml)
  12. customcollected

Sources & evidence

ORD record
ord-7c433e5866b94a3fb0247749a719d86b
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

Loading…