Dimethylformamide → HCID 10332062, compound

Temperature

95 °C

3-Amino-6-bromo-N-methylpyrazine-2-carboxamide (1.34 g, 5.8 mmol) and 3-hydroxyphenylboronic acid (1.2 g, 8.7 mmol) were taken into DMF (10 mL) followed by addition of [1,1′-bis(diphenylphosphinoferrocene]dichloropalladium (II) dichloromethane complex (440 mg, 0.54 mmol) and triethylamine (4.8 mL, 35 mmol). The mixture was heated to 95° C. for 12 hours then cooled to room temperature and diluted with an excess of ethyl acetate. The organic solution was washed with 0.5 M aqueous hydrochloric acid (1×), water (3×) then brine and dried over anhydrous magnesium sulfate. The mixture was then filtered and the organic solution concentrated and the residue purified by silica gel flash chromatography using ethyl acetate:hexanes (3:1) eluent. The pure fractions were combined and concentrated then dried in vacuo to give 3-amino-6-(3-hydroxyphenyl)-N-methylpyrazine-2-carboxamide (1.01 g, 71% yield) as a yellow solid: MS (EI) for C12H13N4O2: 245 (MH+).

1. temperaturethen cooled to room temperature
2. washThe organic solution was washed with 0.5 M aqueous hydrochloric acid (1×), water (3×)
3. dry with materialbrine and dried over anhydrous magnesium sulfate
4. filtrationThe mixture was then filtered
5. concentrationthe organic solution concentrated
6. customthe residue purified by silica gel flash chromatography
7. concentrationconcentrated
8. customthen dried in vacuo

ORD record

ord-1220353a43954ae381a3e0b061f14a37

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07704995B2