Methyl iodide → HCID 57518336, compound

HRID 1408546Notes

Reaction equation

HRID 1408546 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]4[C:19]([CH3:24])=[N:20][CH:21]=[N:22][CH:23]=4)=[O:17])=[CH:11][C:10]=3[F:25])[N:7]=[C:6]([C:26]([F:29])([F:28])[F:27])[CH:5]=2)[CH2:3][CH2:2]1.[H-].[Na+].[CH3:32]I>C1COCC1>[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([N:15]([CH3:32])[C:16]([C:18]4[C:19]([CH3:24])=[N:20][CH:21]=[N:22][CH:23]=4)=[O:17])=[CH:11][C:10]=3[F:25])[N:7]=[C:6]([C:26]([F:28])([F:27])[F:29])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57518335HCID 57518335, compound

Product 1

HCID 57518336HCID 57518336, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-3-fluorophenyl}-4-methylpyrimidine-5-carboxamide (300 mg, 0.74 mmol) was dissolved in THF, cooled to 0° C., added sodium hydride (35 mg, 1.48 mmol) and stirred the mixture for 30 mins at the same temperature. Methyl Iodide (120 mg, 0.84 mmol) was added and heated the reaction mixture to rt. After 3 h, reaction mixture quenched with water. Work up (H2O/AcOEt) and purification afforded the title compound (120 mg) as a pale-yellow solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.99 (s, 1H), 8.41 (s, 1H), 7.46 (t, J 8.1, 1H), 7.08-7.01 (m, 2H), 6.21 (s, 1H), 3.53 (s, 3H), 2.58 (s, 3H), 1.60-1.51 (m, 1H), 0.98-0.88 (m, 2H), 0.70-0.60 (m, 2H). MS (m/z): 418.35 [M−H]−.

Workup

  1. temperatureheated the reaction mixture to rt
  2. waitAfter 3 h
  3. customreaction mixture
  4. customquenched with water
  5. custom(H2O/AcOEt) and purification

Sources & evidence

ORD record
ord-899faa9dfafd4bd8ae992b7ea50e6e19
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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