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

HRID 2252673ノート

反応式

HRID 2252673 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 2 (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 room temperature 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 room temperature 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-6a4f1edc340d4fd39fd7725eb7239b93
出典データセット
uspto-grants-2008_01
特許番号
US07323453B2

反応ノート

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