Acetic Acid → N-[3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

HRID 1040032Notes

Reaction equation

C(O)(=O)C.[Br:5][C:6]1[CH:7]=[C:8]([CH:10]=[C:11]([CH:13]([F:15])[F:14])[CH:12]=1)[NH2:9].Cl[C:17]1[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=1>O1CCOCC1.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([NH:9][C:17]2[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[CH:10]=[C:11]([CH:13]([F:14])[F:15])[CH:12]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Acetic acid (1.01 mL, 17.6 mmol) was added to a mixture of 3-bromo-5-(difluoromethyl)aniline (1.30 g, 5.86 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine (2.14 g, 11.7 mmol) in dioxane (5.0 mL). The mixture was heated to 105° C. for 16 hrs then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with dilute aqueous NaHCO3, brine and dried. The residue was purified by chromatography on silica gel (0-15% ethyl acetate in hexanes) to yield N-[3-bromo-5-(difluoromethyl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (741 mg, 2.01 mmol, 34%).

Workup

temperaturethen cooled to room temperature
washwashed with dilute aqueous NaHCO3, brine
customdried
customThe residue was purified by chromatography on silica gel (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c40b77ecf381443c9872e509a446d0f4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551984B2

Reaction notes

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