N-Iodosuccinimide → (S)-tert-butyl 2-((4-chloro-5-iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate

HRID 1854978ノート

反応式

HRID 1854978 の反応式
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([CH2:11]C)[N:8]([CH2:13][C@@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:4]=2[N:5]=[CH:6][N:7]=1.C1C(=O)N([I:33])C(=O)C1>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([I:33])=[C:9]([CH3:11])[N:8]([CH2:13][C@@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 86714520(S)-tert-butyl 2-((4-chloro-6-ethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate

生成物 1

HCID 86714519(S)-tert-butyl 2-((4-chloro-5-iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the solution of (S)-tert-butyl 2-((4-chloro-6-ethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate (1.0 g, 2.86 mmol, 1.0 eq) in DMF (20 mL), NIS (0.675 g, 3.00 mmol, 1.05 eq) was added at 0° C. The resulted mixture was stirred and warmed to RT for 12 h. Solvent was removed and purified by column chromatography to afford (S)-tert-butyl 2-((4-chloro-5-iodo-6-methyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl)pyrrolidine-1-carboxylate as white solid (1.0 g, 77% in yield) which was converted to the title compound as described in Example 30 above, LCMS m/z 519.1 (M+H)+.

後処理

  1. customSolvent was removed
  2. custompurified by column chromatography
  3. customto afford

出典と根拠

ORDレコード
ord-2ee45b931c144e5ea9be71524e30bd06
出典データセット
uspto-grants-2015_02
特許番号
US08962831B2

反応ノート

読み込み中…