Water → 4-(6-Methoxy-4-methylquinazolin-2-yl)benzoic acid

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To a mixture of 2-chloro-6-methoxy-4-methylquinazoline (Intermediate 9, 350 mg, 1.68 mmol), 4-carboxyphenylboronic acid (418 mg, 2.52 mmol), and K2CO3 (464 mg, 3.36 mmol) in DEGME/H2O (7 mL/1 mL) was added Pd(dppf)Cl2 (30.2 mg, 0.0369 mmol) under N2 atmosphere. Then the mixture was heated to 120° C. for 2 hours. To the reaction mixture was added H2O (30 mL), extracted with EtOAc (15 mL×2), the aqueous layer was acidified with 1M HCl to pH=1-2, filtered and the filter cake was washed with MeOH and dried under high vacuum to give the product (380 mg, yield 78%). 1H NMR (DMSO-d6 400 MHz): δ 8.61 (d, J=8.0 Hz, 2H), 8.10 (d, J=8.4 Hz, 2H), 7.99 (d, J=9.2 Hz, 1H), 7.65 (dd, J=9.2, 2.8 Hz, 1H), 7.54 (d, J=2.8 Hz, 1H), 3.98 (s, 3H), 2.99 (s, 3H).

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