Bromine → 9-Benzyl-8-bromo-2-methoxycarbonylmethylaminoadenine

HRID 1684981

반응식

HRID 1684981 반응식
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][C:11]([NH:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:24]Br>ClCCl>[CH2:1]([N:8]1[C:16]([Br:24])=[N:15][C:14]2[C:9]1=[N:10][C:11]([NH:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24408BromineHCID 230794289-Benzyl-2-methoxycarbonylmethylaminoadenine

생성물 1

HCID 230794409-Benzyl-8-bromo-2-methoxycarbonylmethylaminoadenine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  1. customAfter removing the solvent
  2. additionthe residue was poured into water
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-758fbf6f6f014820a3d3b4f9c3a9604d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148371B2

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