1,2-Dimethoxyethane → 5-Fluoro-6-(2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine

HRID 1811794Notes

Reaction equation

COCCOC.[F:7][C:8]1[C:13](B(O)O)=[CH:12][CH:11]=[CH:10][N:9]=1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH2:25])[C:19]=1[F:26]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:26][C:19]1[C:20]([NH2:25])=[N:21][C:22]([CH3:24])=[N:23][C:18]=1[C:13]1[C:8]([F:7])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

DME (6.00 mL, 57722 μmol) and water (0.6 mL, 3152 μmol) were added to a mixture of 2-fluoropyridin-3-ylboronic acid (666 mg, 4728 μmol), 6-chloro-5-fluoro-2-methylpyrimidin-4-amine (0.5093 g, 3152 μmol), and Pd(Ph3P)4 (364 mg, 315 μmol) under nitrogen. The mixture was sealed and heated at 100° C. for 60 min under microwave irradiation. After cooling, the mixture was diluted with water and the precipitate was collected, washed with DCM, and 5-fluoro-6-(2-fluoropyridin-3-yl)-2-methylpyrimidin-4-amine (418 mg, 60%) was isolated as an off-white powder. LCMS (API-ES) m/z 223 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 8.39 (d, J=4.02 Hz, 1H) 8.18 (t, J=8.03 Hz, 1H) 7.53 (t, J=5.27 Hz, 1H) 7.38 (br. s., 2H) 2.37 (s, 3H).

Workup

customThe mixture was sealed
temperatureAfter cooling
customthe precipitate was collected
washwashed with DCM

Sources & evidence

ORD record: ord-460c343f07e04f73ad296b612e108eb8
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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