N-Iodosuccinimide → N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide

HRID 1984059ノート

反応式

HRID 1984059 の反応式
[Cl:1][C:2]1[C:3]2[CH:17]=[CH:16][NH:15][C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=1.[I:18]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]1[C:3]2[C:17]([I:18])=[CH:16][NH:15][C:4]=2[N:5]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:11])[CH3:12])[N:7]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 11425285N-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide

生成物 1

HCID 15484841N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide (101 g, 0.40 mol) in anhydrous THF (2 L) was treated with N-iodosuccinimide (98.9 g, 0.44 mol, 1.1 eq.) under N2 atmosphere at rt for 40 min. The solvent was evaporated, and the residue was taken up in CH2Cl2 (1.5 L), and washed with Na2SO3 (500 mL×3) and brine (300 mL×3). Evaporated and recrystallizion from MeOH gave the title product as a white powder (122 g, 81% yield, HPLC purity: 98.2%). tR: 6.19 min. 1H-NMR (DMSO-d6) δ 12.65 (br.s, 1H), 10.11 (br. s, 1H), 7.76 (d, 1H), 1.24 (s, 9H).

後処理

  1. customThe solvent was evaporated
  2. washwashed with Na2SO3 (500 mL×3) and brine (300 mL×3)
  3. customEvaporated
  4. customrecrystallizion from MeOH

出典と根拠

ORDレコード
ord-f2f2d28c2b15465fbbf82eb51a194c16
出典データセット
uspto-grants-2009_06
特許番号
US07544672B2

反応ノート

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