Dimethylamine → HCID 86723455, compound

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Reaction Steps

Methanesulfonic anhydride (60.9 mg, 0.35 mmol) was added to a solution of 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-phenyl-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione (Example 12.0) (160 mg, 0.35 mmol) and 2,6-lutidine (0.041 ml, 0.35 mmol) in DCM (16 ml) at 0°. The mixture was stirred at room temperature for 2 hours. The mixture was evaporated under vacuum and the residue redissolved in THF (6 ml). Dimethylamine solution (2M in THF, 6 ml, 12.0 mmol) was added and mixture stirred at room temperature for 1 h, at 35° C. for 16 hours, at 55° C. for 6 hours, again at room temperature for 3 days, then at 55° C. for 4 hours, and finally heated under microwave irradiation at 80° C. for 20 mins. The mixture was evaporated under vacuum. The residue was redissolved in DCM and methanol and loaded onto an Isolute™SCX-2 cartridge. The column was first rinsed with methanol/DCM (1:1, 50 ml) then eluted with 3.5 M NH3/methanol (50 ml). The basic eluent was evaporated under vacuum to afford the title compounds as a mixture of diastereomers

Provenance & Evidence