2-Chloroadenosine → Methane

HRID 1087011Notes

Reaction equation

HRID 1087011 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].[NH2:21][CH2:22][CH2:23][C:24]1[S:25][C:26]([Br:29])=[CH:27][CH:28]=1>>[CH4:2].[Br:29][C:26]1[S:25][C:24]([CH2:23][CH2:22][NH:21][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])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 89742-ChloroadenosineHCID 49619472-(5-Bromothiophen-2-yl)ethan-1-amine

Product 2

HCID 297MethaneHCID 150366292-[2-(5-Bromo-2-thienyl)ethylamino]-adenosine

Conditions

Temperature
140 °C

Procedure

A mixture of 2-chloroadenosine (0.3 g) and 2-(2-aminoethyl)-5-bromothiophene (2.1 g) is stirred under nitrogen at 140° C. over 18 hours. It is concentrated to a small volume under high vacuum (0.1 mm Hg) at 50° C., and the residue is purified by flash chromatography through a silica gel column (25×200 mm) eluting with methylene chloride/ammonia-saturated methanol (9:1). Fractions containing the major product are combined and concentrated to dryness at reduced pressure. The residue is recrystallized from methanol-ether and then from acetonitrile with charcoal to afford 2-[2-(5-bromo-2-thienyl)ethylamino]-adenosine, m.p. 145°-152° dec.

Workup

  1. concentrationIt is concentrated to a small volume under high vacuum (0.1 mm Hg) at 50° C.
  2. customthe residue is purified by flash chromatography through a silica gel column (25×200 mm)
  3. washeluting with methylene chloride/ammonia-saturated methanol (9:1)
  4. additionFractions containing the major product
  5. concentrationconcentrated to dryness at reduced pressure
  6. customThe residue is recrystallized from methanol-ether

Sources & evidence

ORD record
ord-7c0e62ee8fd94cbca74cc6b5313e6607
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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