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 1854978Notes

Reaction equation

HRID 1854978 reaction equation
[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

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-2ee45b931c144e5ea9be71524e30bd06
Source dataset
uspto-grants-2015_02
Patent number
US08962831B2

Reaction notes

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