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With sodium hydride; In tetrahydrofuran; at 0 - 80℃; for 16h;Inert atmosphere;
To a solution of 6-chloropyrazin-2-amine (5 g, 38.6 mmol), sodium hydride (2.316 g, 57.9 mmol) and (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (5.61 g, 42.5 mmol) in Tetrahydrofuran (THF) (50 mL) stirred under nitrogen at 0 C. was added reaction mixture was stirred at 80 C. for 16 h. Reaction mixture was quenched with ice cold water and extracted into ethyl acetate. Organic layer dried over Na2SO4. Solvent evaporated under reduced pressure to afford the crude product. The crude product was added to a silica gel column and was eluted with DCM/MeOH. Fractions with product were combined and evaporated under reduced pressure to give the required product (2.8 g, 11.9 mmol, 31%), LCMS (m/z) 225.9 [M+H]+.
31%
With sodium hydride; In tetrahydrofuran; at 0 - 80℃; for 16h;Inert atmosphere;
To a solution of 6-chloropyrazin-2-amine (5 g, 38.6 mmol), sodium hydride (2.316 g, 57.9 mmol) and (R)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (5.61 g, 42.5 mmol) in Tetrahydrofuran (THF) (50 mL) stirred under nitrogen at 0C was added reaction mixture was stirred at 80 C for 16 h. Reaction mixture was quenched with ice cold water and extracted into ethyl acetate. Organic layer dried over Na2SC"4. Solvent evaporated under reduced pressure to afford the crude product. The crude product was added to a silica gel column and was eluted with DCM/MeOH. Fractions with product were combined and evaporated under reduced pressure to give the required product (2.8g, 1 1.9 mmol, 31%), LCMS (m/z) 225.9 [M+H]+.
(R)-2-chloro-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59.5%
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃; for 12h;
To a stirred solution of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (20 g, 153 mmol) in THF (100 mL) at 0 C was added (R)-(2,2-dimethyl-l,3-dioxolan-4-yl)methanol (24.30 g, 184 mmol), triphenylphosphine (50.2 g, 192 mmol) followed by DEAD (30.3 mL, 192 mmol) and the reaction was stirred at RT for 12 h. (TLC eluting system: 70% EtOAc in pet ether; R/-0.5; UV active). The reaction mixture was quenched with water (100 mL) and extracted into EtOAc (200 mL). Organic layer was separated and dried over anhydrous Na2S04, filtered and filtrate was evaporated to give crude product. The crude was purified by chromatography (Silicagel, eluent: 35% EtOAc in hexane) to afford (R)-2-chloro-5-((2,2- dimethyl-l,3-dioxolan-4-yl)methoxy)pyrimidine (23 g, 91 mmol, 59.5 % yield) as a white solid. LCMS (m/z): 245.06; [M+H]+.
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