Sodium periodate → 6-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde

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Reaction Steps

6-(4-Methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 30, 3.96 g, 11.9 mmol) was suspended in THF (80 mL) and heated with a heat gun to effect dissolution. Similarly, sodium periodate (5.84 g, 27.3 mmol) was heated in water (40 mL) to effect dissolution. The above solutions were combined with vigorous stirring. While the stirred mixture was still at 40° C., osmium(VIII) oxide in ten-butanol (2.90 mL, 2.5%, 0.30 mmol) was added and the mixture was stirred vigorously for 4 h. The reaction mixture was diluted with water (300 mL) and extracted with EtOAc (3×150 mL) and DCM (3×150 mL). The combined organic layers were dried (MgSO4) and concentrated to afford the title compound (4.13 g, 99%) as a black solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 3.77 (s, 3H), 5.80 (s, 2H), 6.83 (d, J=8.66 Hz, 2H), 7.61 (d, J=8.66 Hz, 2H), 8.41 (s, 1H), 9.10 (d, J=2.13 Hz, 1H), 9.26 (d, J=2.13 Hz, 1H), 10.21 (s, 1H). [M+H]=336.2.

Provenance & Evidence