5-Fluoro-6-methoxypyridin-3-amine → HCID 66611960, compound

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Reaction Steps

The title compound was prepared in an analogous manner to that described in Example 164 using 5-fluoro-6-methoxypyridin-3-amine (Anichem) and 4-(6-fluoro-2,4′-bipyridin-5-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine. Purification using an ISCO Combiflash Companion (12 g column and sample loader, 30-100% EtOAc in hexanes over 20 min; the product eluted with 82% EtOAc) afforded the title compound as a brown oil (39.6%). 1H NMR (400 MHz, d6-DMSO) δ 11.86 (s, 1H); 8.91 (d, J=8.2 Hz, 1H); 8.70-8.76 (m, 2H); 8.21 (d, J=2.2 Hz, 1H); 8.09 (dd, J=12.4, 2.2 Hz, 1H); 7.94-7.99 (m, 2H); 7.66 (d, J=8.0 Hz, 1H); 7.26 (dd, J=18.4, 8.6 Hz, 4H); 6.89 (dd, J=18.7, 8.7 Hz, 4H); 4.83 (d, J=9.2 Hz, 4H); 3.95 (s, 3H); 3.74 (s, 3H); 3.70 (s, 3H); 2.59 (s, 3H). m/z (ESI, +ve ion) 645.0 (M+H)+.

Provenance & Evidence