Diisopropylethylamine → 9-Benzyl-2-methoxycarbonylmethylaminoadenine

HRID 1684980

反応式

HRID 1684980 の反応式
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11](Cl)=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21][C:22](=[O:25])[CH2:23][NH2:24].C(N(C(C)C)CC)(C)C>C(O)CCC>[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11]([NH:24][CH2:23][C:22]([O:21][CH3:20])=[O:25])=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

生成物 1

HCID 230794289-Benzyl-2-methoxycarbonylmethylaminoadenine収率 17.2%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
150 °C

実験手順

9-Benzyl-2-chloroadenine (0.30 g, 1.12 mmol), glycine methyl ester hydrochloride (0.72 g, 5.73 mmol) and diisopropylethylamine (1.48 g, 11.47 mmol) were added to n-butanol (10 ml), and the mixture was stirred in an autoclave at 150° C. for 19 hours. The solvent was removed and the residue was poured into water. The solution was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated and the residue was purified by column chromatography to give 9-benzyl-2-methoxycarbonylmethylaminoadenine (0.06 g) as a brown tar. Thus obtained 9-benzyl-2-methoxycarbonylmethylaminoadenine was dissolved in dichloromethane (10 ml) and to the solution was added bromine (0.05 ml) in an ice bath. The mixture was stirred at room temperature for 1 hour. After removing the solvent, the residue was poured into water and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated and the residue was purified by column chromatography to give 9-benzyl-8-bromo-2-methoxycarbonylmethylaminoadenine (0.06 g) as a yellow solid.

後処理

  1. customThe solvent was removed
  2. additionthe residue was poured into water
  3. extractionThe solution was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-770ac510b2ce4e798d8f6746dec3db29
出典データセット
uspto-grants-2012_04
特許番号
US08148371B2

関連ノート

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