Water → 2-Methylpentane

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Reaction Steps

Ethyl 2-(10-(5-chlorofuran-2-yl)-1,3-dimethyl-2,4-dioxo-2,3,4,7,8,10-hexahydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazin-5-yl)thiazole-4-carboxylate (Example 15 Step 1)(72 mg, 0.142 mmol) and lithium hydroxide monohydrate (5.96 mg, 0.142 mmol) were suspended in THF (5 mL) and the mixture stirred at room temperature for 24 hours. Two portions of lithium hydroxide monohydrate (5.96 mg, 0.142 mmol) were added during this period. Water (2 mL) was then added and the mixture stirred for a further 30 mins. The resulting mixture was evaporated under vacuum. The residue was partitioned between water (20 ml) and DCM (20 mL) and brought to pH 1 with HCl(aq). The phases were separated and the aqueous phase was extracted with DCM (2×20 ml). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. The residue was re-suspended in DCM (5 ml) and loaded to a Isolute PE-AX ion exchange cartridge (1 g). The cartridge was eluted with DCM (50 ml), 1:1 MeOH:DCM (20 ml) and 4 M HCl/dioxane. The acidic eluent was evaporated under vacuum and the residue triturated with TBME:iso-hexane to afford the title compound.

Provenance & Evidence