Sodium Carbonate → 4-(2-Chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621391

Reaktionsgleichung

O1CCOCC1.[Cl:7][C:8]1[C:13](B(O)O)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][N:9]=1.Cl[C:20]1[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([NH2:27])[N:21]=1.C([O-])([O-])=O.[Na+].[Na+]>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.O>[Cl:7][C:8]1[C:13]([C:20]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]([NH2:27])[N:21]=2)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

1,4-dioxane (10.00 mL) and water (2.5 mL) were added to a stirred mixture of 2-chloro-5-methoxypyridin-3-ylboronic acid (1.03 g, 5.48 mmol), 4-chloro-6-methyl-1,3,5-triazin-2-amine (0.72 g, 4.98 mmol), Na2CO3 (1.32 g, 12.5 mmol), and Pd(PPh3)4 (0.576 g, 0.1 eq) and the mixture was sealed and heated at 90° C. overnight. After cooling, the mixture was concentrated. Flash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM) provided 4-(2-chloro-5-methoxypyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.644 g, 51%) as a white solid. LCMS (API-ES) m/z 252 (M+H)+; 1H NMR (400 MHz, d6-DMSO) δ 8.24 (d, J=1.17 Hz, 1H) 7.68 (br. s., 2H) 7.65 (d, J=1.17 Hz, 1H) 3.87 (s, 3H) 2.36 (s, 3H).

Aufarbeitung

customthe mixture was sealed
temperatureAfter cooling
concentrationthe mixture was concentrated
customFlash column chromatographic purification (short column, SiO2, pure DCM to 5% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag: ord-acc80c88cf6c4e05b3ecae06d35e0bed
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08772480B2

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