N-bromobutanimide → 5-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1836245ノート

反応式

HRID 1836245 の反応式
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([Br:21])=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 30118937-Deaza-2'-C-methyladenosine

生成物 1

HCID 30118995-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine収率 36.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

To a pre-cooled solution (0° C.) of the compound from Step F of Example 62 (28 mg, 0.10 mmol) in DMF (0.5 mL) was added N-bromosuccinimide (0.018 g, 0.10 mmol) in DMF (0.5 mL) dropwise. The solution was stirred at 0° C. for 20 min, then at rt for 10 min. The reaction was quenched by addition of methanol (4 mL) and evaporated in vacuo. The crude product was purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (13.0 mg) as a colorless solid.

後処理

  1. waitat rt for 10 min
  2. customThe reaction was quenched by addition of methanol (4 mL)
  3. customevaporated in vacuo
  4. customThe crude product was purified on silica gel
  5. additionFractions containing the product
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-044a27a311e045a481805db58816c2d4
出典データセット
uspto-grants-2004_08
特許番号
US06777395B2

反応ノート

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