Methyl iodide → HCID 81935618, compound

HRID 409456Notes

Reaction equation

HRID 409456 reaction equation
FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)C[N:7]([C:29]1[N:34]=[CH:33][C:32]([C:35]2[CH:36]=[N:37][N:38]([CH3:40])[CH:39]=2)=[CH:31][N:30]=1)[C@@H]1CN(C2C(CO)=CN=C(N3CCCCC3)N=2)[C@H](CC)C1.CI.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:40][N:38]1[CH:39]=[C:35]([C:32]2[CH:31]=[N:30][C:29]([NH2:7])=[N:34][CH:33]=2)[CH:36]=[N:37]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59614410HCID 59614410, compound

Product 1

HCID 81935618HCID 81935618, compoundYield 142.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-2-piperidin-1-yl-pyrimidin-5-yl]-methanol (40 mg, 0.06 mmol) and methyl iodide (0.004 mL, 0.7 mmol) in 1 mL of DMF is added sodium hydride (2.8 mg, 0.07 mmol) and stirred at room temperature for 1 day. Saturated NH4Cl aqueous solution is added at room temperature and then extracted twice with 50 mL of EtOAc. The combined organic layer is washed with brine, dried over Na2SO4 and concentrated. Column chromatography (eluent: hexane/EtOAc) give (3,5-bis-trifluoromethyl-benzyl)-[3S,5R)-5-ethyl-1-(5-methoxymethyl-2-piperidin-1-yl-pyrimidin-4-yl)-pyrrolidin-3-yl]-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine (15 mg, 37% yields) as white solid.

Workup

  1. extractionextracted twice with 50 mL of EtOAc
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bdf16eaff7824eaeac72c4d9480f2b72
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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