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

HRID 1984059Notes

Reaction equation

HRID 1984059 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-f2f2d28c2b15465fbbf82eb51a194c16
Source dataset
uspto-grants-2009_06
Patent number
US07544672B2

Reaction notes

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