Triethylamine → N-[2-(2-methyl-1H-imidazol-1-yl) ethyl]adenosine, hydrochloride

HRID 345169

Reaction equation

HRID 345169 reaction equation
[CH:1]1[N:6]=[C:5]([Cl:7])[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[CH3:20][C:21]1[N:22]([CH2:26][CH2:27][NH2:28])[CH:23]=[CH:24][N:25]=1.C(N(CC)CC)C>C(O)C>[ClH:7].[CH3:20][C:21]1[N:22]([CH2:26][CH2:27][NH:28][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[CH:23]=[CH:24][N:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 31574802-(2-Methyl-1H-imidazol-1-yl)ethan-1-amine

Product 1

HCID 131717028N-[2-(2-methyl-1H-imidazol-1-yl) ethyl]adenosine, hydrochlorideYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension was prepared containing 1.64 g (5.74 mmol) of 6-chloropurine riboside in 12 ml of absolute ethanol. To the solution was added 0.72 g (5.7 mmol) of 2-(2-methyl-imidazol-1-yl) ethylamine (prepared in accordance with Z.Obsch. Chim. 11, 545 (1941); Chem Ab. 1941 6938) and 0.81 g (8.0 mmol) of triethylamine. The reaction mixture was heated under reflux for 77 hours. The solvent was removed in vacuo and chromatography of the residue on silica gel was performed by eluting with a mixture of 22 parts methanol, 88 parts methylene chloride, and one part ammonium hydroxide. The title compound was obtained as the free base yielding 1.2 g (55% yield). This material was converted to the hydrochloride salt by suspending in 20 ml of water at 0° and adding 1 normal hydrochloric acid until a pH of 2.6 was attained. The solution was frozen and lyophilized giving a white powder which was passed through a column of cellulose powder eluting with a mixture of 85 parts n-butanol and 15 parts water. The appropriate fractions were combined and concentrated to give a glass which was azeotroped twice with water and then dissolved in water, frozen and lyophilized giving 1.1 g (44% yield) of the title compound as a white powder.

Workup

  1. customA suspension was prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 77 hours
  4. customThe solvent was removed in vacuo and chromatography of the residue on silica gel
  5. washby eluting with a mixture of 22 parts methanol, 88 parts methylene chloride, and one part ammonium hydroxide

Sources & evidence

ORD record
ord-ae310559ff934207b8431f6e15fa8d39
Source dataset
uspto-grants-1991_10
Patent number
US05055569

Linked notes

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