Isopropylamine → 4'-Cyclopropylmethyl-N2'-isopropyl-N2-pyridin-4-yl-[4,5']bipyrimidinyl-2,2'-diamine

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Reaction Steps

To a solution of 4′-(cyclopropylmethyl)-2′-(methylsulfanyl)-N-pyridin-4-yl-4,5′-bipyrimidin-2-amine (11) (35 mg, 0.096 mmol) in DMSO (1 mL), isopropylamine (24.55 μl, 0.287 mmol) was added and the reaction was microwaved for 20 minutes at 160° C. The crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 10% MeOH/DCM] to afford the title compound as a pale-yellow solid (13.67 mg, 39.6% yield). 1H NMR (400 MHz, MeOD) δ ppm 0.04-0.17 (m, 2 H) 0.31-0.50 (m, 2 H) 0.97-1.17 (m, 1 H) 1.27 (d, J=6.57 Hz, 6 H) 2.88 (d, J=7.07 Hz, 2 H) 4.22 (ddd, J=13.01, 6.44, 6.32 Hz, 1 H) 7.10 (d, J=5.05 Hz, 1 H) 7.84 (d, J=7.07 Hz, 2 H) 8.30 (d, J=6.57 Hz, 2 H) 8.42 (s, 1 H) 8.55 (d, J=5.05 Hz, 1 H). HRMS (ES+) for C20 H23N7.H+ [MH+]: calcd, 362.2093. found, 362.2083. UV-LC: 100% UV purity at 254/214 nm; tR=3.39 minutes over 7.75 minutes.

Provenance & Evidence