Sodium Carbonate → HCID 54741096, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-(2-(3-fluorophenyl)-5-hydroxy-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)acetate. To a mixture of tert-butyl 2-(2-chloro-5-hydroxy-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)acetate (100 mg, 1 eq., Method 10), Pd(dppf)Cl2 (0.05 eq.), 3-fluorophenylboronic acid (3.0 eq., available from Aldrich (Milwaukee, Wis.)) in degassed dioxane (4 mL) was added degassed aqueous Na2CO3 (2M, 3 eq.) in a sealed tube. The mixture was stirred overnight at 80° C. The mixture was then cooled to room temperature and diluted with water. The phases were separated and extracted with more CH2Cl2. The combined organic phases were washed with water and brine, dried over Na2SO4 and concentrated. The residue was dissolved in DMA and purified on reversed phase HPLC to give the title compound (48 mg, 41%) as a light brown solid. C21H21FN4O5 (428.4). APCI-MS: 429 ([M+H]+), 373 ([M-(t-Bu)+H]+). 1H-NMR (DMSO-d6): δ 10.21 (br s, 1H), 9.39 (s, 1H), 8.40 (d, J=7.8, 1H), 8.25 (d, J=9.3, 1H), 7.66 (q, J=8.1, 1H), 7.49 (dt, J=8.5, 2.5, 1H), 4.13 (d, J=5.7, 2H), 3.55 (s, 3H), 1.46 (s, 9H).

Provenance & Evidence