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. 2017 Mar 15;8(5):1069–1092. doi: 10.1039/c7md00052a

Scheme 2. Synthesis of diaminoquinazolines in Table 3. Reagents and conditions: (i) benzyl bromide, K2CO3, DMF, 0 °C – RT, 18 h; (ii) HNO3, Ac2O, RT, 18 h; (iii) Fe, NH4Cl, i-PrOH/H2O, reflux, 18 h; (iv) a) NaOCN, H2O/AcOH, RT, 18 h; b) NaOH, MeOH, reflux, 6 h; (v) POCl3, DIEA, acetonitrile, reflux, 6 h; (vi) various amines, Et3N (or DIEA), THF (or DMF), RT, 18–24 h; (vii) various amines (5–10 equiv.), microwave, toluene (or neat), 130–185 °C, 30–50 min or i-PrOH, 4 M HCl/dioxane, microwave, 160 °C, 15 min; (viii) TFA, reflux, 3 h; (ix) K2CO3 (or Cs2CO3), DMF, alkyl halides, 3–18 h 80 °C or PPh3, DIAD, THF, 20 h, RT.

Scheme 2