Sodium Carbonate → HCID 51352116, compound

Participants

Reaction Conditions

Reaction Steps

Combined 2-chloro-5-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.201 g, 0.545 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (0.166 g, 0.599 mmol), PdCl2(dppf) (0.080 g, 0.109 mmol), sodium carbonate (saturated in water) (1.5 ml, 0.545 mmol) and dioxane (3 ml). The suspension was heated by microwave irradiation at 100° C. for 45 minutes. The reaction mixture was filtered via syringe filter and purified the title compound 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. Product containing fractions were concentrated in vacuo to remove about ½ of the total volume and allowed t and let sit at room temperate. After 3 days, the sample was concentrated and purified by HPLC (15-25% of AcCN [containing 0.035% TFA] in water [containing 0.05% TFA], Phenomenex Gemini 5 μm C18, 75×30 mm column) and the product containing fractions were combined, concentrated in vacuo and lyophilized, affording the title compound (27.9 mg, 11.5% yield) as a pale green solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.46 (m, 3H) 2.66 (s, 3H) 3.23-3.36 (m, 1H) 3.36-3.46 (m, 1H) 3.59 (t, J=12.00 Hz, 1H) 3.66-3.74 (m, 1H) 3.74-3.87 (m, 2H) 3.88-4.66 (m, 7H) 6.12 (br. s., 1H) 7.44-7.58 (m, 2H) 8.09-8.23 (m, 2H) 8.28-8.45 (m, 1H) 8.73-8.87 (m, 1 H). MS [M+H] found 443.4.

Provenance & Evidence