Sodium Chloride → HCID 51352112, compound

Participants

Reaction Steps

A microwave vial equipped with a magnetic stirrer was added crude (6aS,7S)-2-chloro-5-(cyclopropylmethyl)-6a,7-dimethyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (98 mg, 0.304 mmol), 1,4-dioxane (1.5 ml), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (126 mg, 0.455 mmol), saturated NaHCO3 (0.500 mL), and PdCl2(dppf) (11.11 mg, 0.015 mmol). The reaction was irradiated in the microwave at 100° C. for 40 minutes. The reaction solution was poured into saturated NaCl and extracted with ethyl acetate three times. The organic layers were collected, dried over Na2SO4, filtered and concentrated in-vacuo to give a brown residue. The residue was purified by preparative HPLC (eluting with 20-30% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column to afford the title compound (6.8 mg, 0.016 mmol, 5.13% yield) as a light brown solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.46 (m, 2H) 0.60 (m, 2H) 1.20-1.25 (m, 1H) 1.41 (d, J=6.6 Hz, 3H) 1.92 (s, 3H) 2.81 (s, 3H) 3.53-3.67 (m, 1H) 3.79-3.87 (m, 1H) 3.91 (d, J=7.0 Hz, 2H) 3.99-4.11 (m, 1H) 4.27 (d, J=6.6 Hz, 1 H) 4.87-5.00 (m, 1H) 7.65 (d, J=8.8 Hz, 2H) 7.97 (s, 1H) 8.11 (d, J=8.8 Hz, 2H). MS [M+H] found 437.

Provenance & Evidence