Acetic Acid → 5-Methyl-3-(4-(trifluoromethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-2-amine

HRID 1912966Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([NH2:16])=[N:12][NH:13][C:14]=2[NH2:15])=[CH:6][CH:5]=1.CN(C)[CH:21]=[CH:22][C:23](=O)[CH3:24].C(O)(=O)C>C(O)C>[CH3:24][C:23]1[CH:22]=[CH:21][N:13]2[N:12]=[C:11]([NH2:16])[C:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:17])[F:18])=[CH:5][CH:6]=3)=[C:14]2[N:15]=1

Participants

Conditions

Temperature: -10 °C

Procedure

The product from Example 1B (200 mg, 0.775 mmol) was charged to a microwave vial with a stir bar. A solution of 4-(dimethylamino)but-3-en-2-one (175 mg, 1.55 mmol) in ethanol (2 mL) was added, and the mixture was stirred at room temperature as acetic acid (25 ΞL, 0.437 mmol) was added. The solution was irradiated in the microwave at 150° C. for 35 minutes, then cooled to room temperature and finally to −10° C. The precipitate was removed by filtration, and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc, 70:30-40:60) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.47 (s, 3H), 5.71 (s, 2H), 6.69 (d, J=7.1 Hz, 1H), 7.39 (d, J=8.1 Hz, 2H), 7.87-7.98 (m, 2H), 8.62 (d, J=7.1 Hz, 1H).

Workup

additionwas added
customThe solution was irradiated in the microwave at 150° C. for 35 minutes
customThe precipitate was removed by filtration
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc, 70:30-40:60)

Sources & evidence

ORD record: ord-ebfdfb1250144c7fb33d5c5fd6b6a8ad
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609669B2

Reaction notes

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