Methyl iodide → HCID 67326839, compound

HRID 1500749Notes

Reaction equation

HRID 1500749 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[N:11]=[CH:12][C:13]([C:14]3[N:19]=[C:18]([NH:20][C@@H:21]4[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]4)[CH:17]=[CH:16][N:15]=3)=[C:7]2[CH:6]=1)#[N:4].[CH3:34]I>CN(C)C=O>[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[N:11]=[CH:12][C:13]([C:14]3[N:19]=[C:18]([N:20]([CH3:34])[C@@H:21]4[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]4)[CH:17]=[CH:16][N:15]=3)=[C:7]2[CH:6]=1)#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67326745HCID 67326745, compound

Product 1

HCID 67326839HCID 67326839, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 102 mg, 2.55 mmol) was added to a cooled (0° C.) solution of tert-butyl (3R)-3-{[2-(5-cyanopyrazolo[1,5-a]pyridin-3-yl) pyrimidin-4-yl]amino}piperidine-1-carboxylate (Preparation 7a, 0.83 g, 1.98 mmol) in NIP-dimethylformamide (5 mL) and the reaction mixture was stirred at the same temperature for 30 minutes. Methyl iodide (0.135 mL, 2.17 mmol) was then added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent was evaporated to give the title compound (0.39 g, 80%) as a beige solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 hours
  2. concentrationThe solvent was concentrated in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b8b01be62e634357ae65c309a0a7948c
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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