Trifluoroacetic acid → (R)-2,5-di(1H-indol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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Reaction Steps

(R)-tert-Butyl 4-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-1H-indole-1-carboxylate (PREPARATION x65, 9 mg, 0.017 mmol) was dissolved in CH2Cl2 (1 mL) and trifluoroacetic acid (1 mL) and the mixture was stirred at room temperature for 30 minutes. The material was then concentrated in vacuo and the product was purified by LC/MS using a 20-45% CH3CN gradient in H2O (with 0.035% TFA). The pure fractions were combined and lyophilized to afford a TFA salt of the title compound as a yellow solid (2 mg, 28%). 1H NMR (400 MHz, CD3CN) δ ppm 3.36-3.61 (m, 3 H), 3.68-3.87 (m, 2 H), 3.97-4.07 (m, 1 H), 4.07-4.20 (m, 2 H), 4.91-5.00 (m, 1 H), 6.28-6.38 (m, 1 H), 6.98-7.09 (m, 2 H), 7.12-7.17 (m, 1 H), 7.22-7.35 (m, 3 H), 7.44-7.51 (m, 2 H), 7.65-7.75 (m, 2 H), 9.57-9.67 (m, 1 H), 9.67-9.81 (m, 1 H); ESI-MS m/z [M+H]+ calc'd for C25H22N6O, 423.19; found 423.3.

Provenance & Evidence