2-Chloroadenosine → HCID 15036649, compound

HRID 1087020Notes

Reaction equation

HRID 1087020 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].[O:21]1[CH2:26][CH2:25][CH:24]([CH2:27][CH2:28][NH2:29])[CH2:23][CH2:22]1>>[O:21]1[CH2:26][CH2:25][CH:24]([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])[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 89742-ChloroadenosineHCID 27731982-(Oxan-4-yl)ethan-1-amine

Product 1

HCID 15036649HCID 15036649, compound

Procedure

A mixture of 2-chloroadenosine (0.3 g) and 2-(tetrahydropyran-4-yl)ethylamine (1.15 g) is stirred under nitrogen at 140° for 6 hours. The mixture is concentrated to dryness at reduced pressure, the residue is dissolved in ethanol, the solution is treated with propylene oxide (2 ml) and stirred overnight. It is concentrated to dryness and chromatographed through a 25×180 mm column of silica gel, with methylene chloride and ammonia-saturated methanol (9:1) as eluent. The fractions containing the desired product are combined and concentrated at reduced pressure. The residue is dissolved in absolute ethanol and treated with ethanolic hydrogen chloride to form the hydrochloride salt of 2-[2-(tetrahydropyran-4-yl)ethyl-amino]adenosine; [alpha]D25 -13.6° (DMSO); m.p. 120°-130° dec.

Workup

  1. concentrationThe mixture is concentrated to dryness at reduced pressure
  2. dissolutionthe residue is dissolved in ethanol
  3. additionthe solution is treated with propylene oxide (2 ml)
  4. stirringstirred overnight
  5. concentrationIt is concentrated to dryness
  6. customchromatographed through a 25×180 mm column of silica gel, with methylene chloride and ammonia-saturated methanol (9:1) as eluent
  7. additionThe fractions containing the desired product
  8. concentrationconcentrated at reduced pressure
  9. dissolutionThe residue is dissolved in absolute ethanol
  10. additiontreated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-e329001ff8714ea18a2be184fb59bae5
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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