Trifluoroacetic acid → 4(1H)-Pteridinone, 2-amino-5,6,7,8-tetrahydro-6-(methoxymethyl)-

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Reaction Steps

The pteridinone (0.5 g, 2.4×10-3 mol) previously prepared, vide supra, was hydrogenated under 1 atm of H2 in 30 mL of distilled trifluoroacetic acid over 0.02 g of PtO2 for an hour. The mixture was diluted with 25 mL of 6N HCl, filtered, and evaporated. The crude product, the tetrahydro compound, was recrystallized twice from 6N HCl/acetonitrile to give 2-amino-5,6,7,8-tetrahydro-6-methoxymethyl-4(3H)-pteridinone as a light brown solid (0.6 g, 85%): UV (0.1N HCl) λmax 215.5 nm (19800), 264 nm (19900); IR(KBr) 3300, 1665, 1570, 1540, 1470, 1365, 1300, 1150, 1110, 1005, 955, and 750 cm-1 ; NMR(DMSO-d6) 3.29δ (s, OMe), 3.4 (m, CH's), 3.6 (br s, OCH2), 8.0 (NH); anal. Calcd. for C8H13N5O2.2HCl.1/2H2O: C, 32.78; H, 5.50; N, 23.89; Cl, 24.19. Found: C, 32.75; H, 5.54; N, 23.80; Cl, 24.21.

Provenance & Evidence