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

HRID 1984059노트

반응식

HRID 1984059 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f2f2d28c2b15465fbbf82eb51a194c16
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544672B2

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