Potassium Carbonate → 7-benzyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-8-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200621ノート

反応式

HRID 2200621 の反応式
[Cl:1][C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15](Cl)=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[NH:7][C:6](=[O:20])[N:5]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:4]=2[N:3]=1.Br[CH2:30][CH2:31][CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([N:10]1[C:9]2[C:8](=[O:19])[N:7]([CH2:30][CH2:31][CH2:32][O:33][Si:34]([C:37]([CH3:38])([CH3:40])[CH3:39])([CH3:35])[CH3:36])[C:6](=[O:20])[N:5]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:4]=2[N:3]=[C:2]1[Cl:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 904024848-chloro-7-(4-chlorobenzyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione

生成物 1

HCID 904034287-benzyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-8-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione収率 103.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a solution of 8-chloro-7-(4-chlorobenzyl)-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (250 mg, 0.568 mmol) in DMF (30 mL) was added (3-bromopropoxy)(tert-butyl)dimethylsilane (0.2 g, 0.794 mmol), followed by potassium carbonate (160 mg, 1.13 mmol). The mixture was stirred at 70° C. overnight. The reaction was cooled and partitioned between ethyl acetate and water. The combined organic phase was washed with brine, dried over sodium sulfate, and concentrated to give 7-benzyl-1-(3-(tert-butyldimethylsilyloxy)propyl)-8-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-1H-purine-2,6(3H,7H)-dione (340 mg, 97.4% yield) as colorless oil. LCMS retention time 4.675 min; LCMS MH+ 613.

後処理

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-210a969844a6453892e3079f15d62233
出典データセット
uspto-grants-2016_06
特許番号
US09359359B2

反応ノート

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