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

HRID 345168

反応式

HRID 345168 の反応式
[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.[N:20]1([CH2:25][CH2:26][NH2:27])[CH:24]=[CH:23][N:22]=[CH:21]1.C(N(CC)CC)C>C(O)C>[ClH:7].[N:20]1([CH2:25][CH2:26][NH:27][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:24]=[CH:23][N:22]=[CH:21]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 4306672-(1H-imidazol-1-yl)ethanamine

生成物 1

HCID 9930713N-[2-(1H-imidazol-1-yl)ethyl]adenosine, hydrochloride収率 59%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspension of 6-chloropurine riboside (1.63 g, 5.69 mmol) in 12 ml of absolute ethanol was added 0.63 g (5.7 mmol) of 2-(imidazol-1-yl)ethylamine (prepared in accordance with Z.Obsch. Chem. 9 1933 (1939); Chem Ab. 1940 2466) plus 0.80 g (8.0 mmol) of triethylamine. The reaction mixture was heated under reflux for 77 hours. Removal of the solvent in vacuo and chromatography of the residue on silica gel eluting with a mixture of MeOH (NH3) and dichloromethane in a ratio of 14:86 gave the free base of the title compound in an amount of 1.2 g (59% yield). The material was converted to the hydrochloride salt by suspending the material in 20 ml of water at 0° centigrade and adding 1N hydrochloric acid until a pH of 2.6 was attained. The solution was frozen and lyophilized to 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 yielding 0.97 g of the title compound (41% yield) as a white powder.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 77 hours
  3. customRemoval of the solvent in vacuo and chromatography of the residue on silica gel eluting
  4. additionwith a mixture of MeOH (NH3) and dichloromethane in a ratio of 14:86

出典と根拠

ORDレコード
ord-43fb8a2a8fb04b489381b4b7dd184e51
出典データセット
uspto-grants-1991_10
特許番号
US05055569

関連ノート

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