Nitrogen → 5-(3-Chloro-2-methoxy-4-pyridinyl)-N4-(4,4-dimethylcyclohexyl)-2,4-pyrimidinediamine

温度

80 °C

To a 50 mL single-necked round bottom flask were placed compound 326 (0.80 g, 2.3 mmol), 3-chloro-2-methoxypyridin-4-ylboronic acid (1.3 g, 6.9 mmol), and trans-dichlorobis(triphenyl-phosphine)palladium (ii) (0.16 g, 0.23 mmol). The flask was subjected to 3 cycles of evacuation and back-filling with N2. 1,4-Dioxane (12 mL) was added followed with sodium carbonate (2 N aqueous solution) (5.8 mL, 12 mmol). The resulting mixture was heated in an oil bath at 80° C. for 18 h. Upon workup, the mixture was poured into ice and saturated NaHCO3 aqueous solution and extracted with ethyl acetate (3×). The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was subjected to combi-flash column chromatography (methanol/DCM) to give compound 332 (0.68 g, 81% yield) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.09 (1 H, d, J=5.1 Hz), 7.48 (1 H, s), 6.92 (1 H, d, J=5.1 Hz), 6.13 (2 H, s), 5.79 (1 H, d, J=8.3 Hz), 3.91-4.02 (4 H, m), 1.26-1.63 (6 H, m), 1.13-1.25 (2 H, m), 0.88 (6 H, d, J=9.8 Hz). LCMS-ESI (POS), M/Z, M+1: Found 362.0.

1. customTo a 50 mL single-necked round bottom flask were placed
2. extractionextracted with ethyl acetate (3×)
3. dry with materialThe combined organics were dried over Na2SO4
4. concentrationconcentrated in vacuo

ORDレコード

ord-23a24b9ba7c242caa6b65486b060f131

出典データセット

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08980903B2