Potassium Carbonate → 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine

HRID 537490Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:19])([F:18])[C:13]1[CH:14]=[N:15][NH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N+:8]([C:5]1[CH:4]=[N:3][C:2]([N:15]2[CH:14]=[C:13]([C:12]([F:19])([F:18])[F:11])[CH:17]=[N:16]2)=[N:7][CH:6]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

A round bottom flask was charged with 2-chloro-5-nitropyrimidine (2.50 g, 15.7 mmol), 4-(trifluoromethyl)-1H-pyrazole (2.35 g, 17.2 mmol), K2CO3 (4.33 g, 31.3 mmol) and acetonitrile (39 mL). The reaction was heated at 80° C. for 2 hours. Potassium carbonate filtered off with a büchner funnel and acetonitrile removed under reduced pressure. The crude material was dissolved in ethyl acetate and transferred to a separatory funnel. Organics washed with water (3×), with brine (1×), dried over sodium sulfate, filtered and concentrated to afford the raw material. Purification by silica gel flash chromatography (ethyl acetate/heptane) provide 5-nitro-2-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyrimidine (1.95 g, 49%) as a yellow solid. MS (M+1): 259.2.

Workup

filtrationPotassium carbonate filtered off with a büchner funnel
customacetonitrile removed under reduced pressure
dissolutionThe crude material was dissolved in ethyl acetate
customtransferred to a separatory funnel
washOrganics washed with water (3×), with brine (1×)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto afford the raw material
customPurification by silica gel flash chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record: ord-65cfc85a93b442039175e7582c2fe8f6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859591B2

Reaction notes

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