N-Methyl-4-anisidine → N-{4-[(4-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

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Using the general procedure described above, the reaction of 6 (180 mg, 0.59 mmol) and 4-methoxy-N-methylaniline (612 mg, 4.46 mmol) was run for 120 hours, to provide 88 mg of 11 as a brown solid in 37% yield. TLC Rf 0.57 (chloroform-methanol 15:1); mp 288.5-289.4° C.; 1H NMR (DMSO-d) δ 1.26 (s, 9H, C(CH3)3), 3.60 (s, 3H, OCH3), 3.69 (s, 3H, NCH3), 5.87-7.33 (m, 8H, Ar—H), 9.58 (s, 1H, 2-NH, exch), 11.88 (s, 1H, 9-NH, exch).

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