2,6-Di-tert-butyl-4-methylphenol → HCID 68709855, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(2-amino-5-bromo-pyrimidin-4-yl)-4-iodo-2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (XXVIIA, R2=phenyl, R3=COOEt, 0.099 mmol) in dioxane (4 mL), under argon, vinyltributyltin (0.099 mmol), 2,6-di-tert-butyl-4-methylphenol (0.0045 mmol) and Pd(Ph3P)4 (0.01 mmol) were added. The reaction mixture was heated at 110° C. for 3 h, cooled to rt, the precipitate filtered through a celite pad and the resulting solution evaporated to dryness. The residue was chromatographed on silica gel (eluant: AcOEt/hexane 4:1) affording the title compound (0.03 mmol, 30% yield), ESI (+) MS: m/z 333 (MH+). 1H NMR: 1.20 (t, J=7.03, 3H), 4.19 (q, J=7.03, 2H), 6.55 (bs, 2H), 7.50 (d, J=8.60, 1H), 7.53-7.70 (m., 5H), 7.90 (d, J=8.60, 1H), 9.07 (s, 1H), 12.93 (s, 1H), and 5-amino-8-methylene-2-phenyl-3,8-dihydro-3,4,6-triaza-cyclopenta[a]indene-1-carboxylic acid ethyl ester (0.024 mmol) (XXVIII, R2=phenyl, R3=COOEt), ESI (+) MS: m/z 333 (MH+). 1H NMR: 1.14 (t, J=7.07 Hz, 3H), 4.16 (q, J=7.07 Hz, 2H), 6.02 (d, J=1.32, 1H), 6.43 (d, J=1.32, 1H), 6.57 (bs, 2H), 7.40-7.46 (m, 2H), 7.52-7.66 (m, 3H), 8.44 (s, 1H), 12.74 (s, 1H).

Provenance & Evidence