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2-tert-butyl-4-hydroxy-6-cyclobutyl-pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85.7%
With sodium methylate; In methanol; at 10 - 20℃;
a.1.2: 2-terf-Butvl-4-hvdroxv-6-cvclobutvl-pvrimidine; 9.2 g of tert-butyl amidinium chloride (67.3 mmol, Maybridge) and 12.6 g of methyl-2-cyclobutanoyl acetate (80.7 mmol) were dissolved/suspended in 100 ml of methanol. 14.5 g of sodium methanolate (268.4 mmol) were added in portions to the solution at 10C. The suspension was then stirred at room temperature overnight. The reaction mixture was concentrated to roughly half the volume and filtered. The filtrate was extracted with water and dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and then concentrated to dryness. The residue was stirred with acetone and the precipitate was collected by filtration. Yield: 11.9 g (85.7 %).MS (ESI) m/z: 207.2 [M+H]+
85.7%
With sodium methylate; In methanol; at 10 - 20℃;
a.1.2: 2-terf-Butyl-4-hydroxy-6-cyclobutyl-pyrimidine; 9.2 g of te/t-butyl amidinium chloride (67.3 mmol, Maybridge) and 12.6 g of methyl-2- cyclobutanoyl acetate (80.7 mmol) were dissolved/suspended in 100 ml of methanol. 14.5 g of sodium methanolate (268.4 mmol) were added in portions to the solution at 1O0C. The suspension was then stirred at room temperature overnight. The reaction mixture was concentrated to roughly half the volume and filtered. The filtrate was ex- traded with water and dichloromethane. The organic phase was dried over magnesium sulfate, filtered, and then concentrated to dryness. The residue was stirred with acetone and the precipitate was collected by filtration. Yield: 1 1.9 g (85.7 %). EPO <DP n="20"/>MS (ESI) m/z: 207.2 [M+H]+
2-tert-butyl-4-hydroxy-6-cyclopropyl-pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
67.2%
With sodium methylate; In methanol; at 10 - 20℃;
a.2.2: 2-terf-Butvl-4-hvdroxv-6-cyclopropvl-pyrimidine; 16.3 g tert-butyl amidinium chloride (119.6 mmol, Maybridge) were dissolved/suspended in 350 ml of methanol at room temperature. 30.4 g of sodium methanolate (562.8 mmol) were added in portions to the solution at 10C,. After stirring for 30 minutes, a solution of 20 g of methyl-2-cyclopropanoyl acetate (140.7 mmol) in 150 ml of methanol was added over 2 h. The suspension was then stirred at room temperature overnight, concentrated to roughly half the volume, and filtered. 200 ml of dichloromethane were added to the filtrate and theorganic layer was washed 3 times with water. The aqueous phases were combined. The aqueous phase was adjusted to pH 3 with aq. HCI, whereby a white precipitate was formed. The precipitate was collected by filtration, redissolved in dichloromethane, dried over magnesium sulfate and filtered. The solvent was concentrated to dryness to yield 14.8 g (67.2 %) of the title compound.MS (ESI) m/z: 193.1 [M+H]+
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