2,4-Dichloropyrimidine → HCID 10323158, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of the title compound of Example 158 (100 mg, 0.27 μmol) in THF (3 mL) was added a solution of 1M potassium t-butoxide in THF (320 mL, 0.32 μmol 1.2 eq.), followed by a solution of 2,4-dichloropyrimidine (40 mg, 0.27 μmol) in DMF (1 mL). The mixture was stirred at 50° C. for 30 min. After cooling to RT, the mixture was diluted with diethyl ether and washed with 6N HCl. The aqueous layer was made basic with 5N NaOH and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Purification by silica gel chromatography yielded the title compound (55 mg, 42%) as an off-white solid. 1H NMR (300 MHz, d6-DMSO): 9.81 (s, 1H), 8.79 (d, J=2.2, 1H), 7.69 (d, J=5.7, 1H), 7.66 (s, 1H), 7.60 (d, J=4.9, 2H), 7.54–7.51 (m, 2H), 7.28–7.22 (m, 3H), 4.00 (s, 3H), 3.22 (q, J=7.3, 2H), 1.13 (t, J=7.3, 3H). MS (ES+, m/z)=487,489 (m+H)+.

Provenance & Evidence