Sodium Hydroxide → (2,6-Dichloropyrimidin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamine

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Reaction Steps

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (500 mg, 1.83 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 4-amino-2,6-dichloropyrimidine (450 mg, 2.75 mmol) and powdered NaOH (220 mg, 5.50 mmol) at rt. Work-up of the mixture as described in example 2, gave the product as an off-white color solid (500 mg, 68%), mp 268-270° C. 1H NMR (400 MHz, CDCl3): δ 8.67 (1H, s), 8.64 (1H, s), 8.23 (1H, s, exchangeable with D2O), 3.11 (2H, t, J=6.1 Hz), 2.97 (2H, t, J=6.1 Hz), 2.01-2.06 (2H, m), 1.92-1.98 (2H, m); 13C NMR (100 MHz, CDCl3): δ 172.9, 162.7, 160.0, 159.2, 152.4, 151.0, 142.7, 126.3, 121.3, 107.8, 28.3, 28.2, 22.7, 22.4; LC-MS (negative ion mode): m/z 396, 398, 400, 402 (M−H)−.

Provenance & Evidence