2,6-Di-tert-butylpyridine → HCID 136337164, compound

Participants

Reaction Steps

The titled compound was prepared in a manner analogous to Example 27, steps C-D, using 4-ethynylaniline in step C, and with the addition of 4.0 equivalents of 2,6-di-tert-butylpyridine in step D. The crude product contained a 2.4:1 mixture of the titled product and 1-[6-(1-chloro-vinyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, ethyl ester. A portion of this mixture was purified by HPLC to afford 1-(6-ethynyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid, ethyl ester. MS (ESI): mass calcd. for C16H12N4O3, 308.1; m/z found, 309.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.98 (br s, 1H), 8.95 (s, 1H), 8.27 (s, 1H), 8.07 (s, 1H), 7.82 (dd, J=8.4, 1.9 Hz, 1H), 7.72-7.54 (m, 1H), 4.31 (s, 1H), 4.23 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 3H).

Provenance & Evidence