Methyl iodide → HCID 57518336, compound

HRID 388841Notes

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

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

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

Sources & evidence

ORD record: ord-756977b661d34c37a489ed0f39eec180
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377970B2

Reaction notes

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