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2.8 6 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide,Then 0.3 g (12 mmol) sodium hydride was added.The mixture was stirred for 1 hour,Then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added.After stirring at room temperature for 24 hours,Carefully hydrolyze with 10 ml of water,The pH was adjusted to 5 with acetic acid,The solvent was removed by distillation under high vacuum.The residue was placed in 100 ml of ethyl acetate,Wash with water,And dried over magnesium sulfate,The solvent was distilled off.The residue was mixed with 10 ml of ether,The resulting precipitate was collected by suction filtration.After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C.
In N-methyl-acetamide; water; ethyl acetate;
Example 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h, cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained. Melting point 81 C.
In N-methyl-acetamide; water; ethyl acetate;
EXAMPLE 3 Methyl 2-(4,6-dimethoxy-pyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate 2.86 g (10 mmol) of <strong>[178306-47-3]methyl 2-hydroxy-3-methoxy-3,3-diphenylpropionate</strong> were dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride was added. The mixture was stirred for 1 h. and then 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine were added. After stirring at room temperature for 24 h., cautious hydrolysis was carried out with 10 ml of water, the pH was adjusted to 5 with acetic acid, and the solvent was removed by distillation under high vacuum. The residue was taken up in 100 ml of ethyl acetate, washed with water and dried over magnesium sulfate, and the solvent was distilled out. The residue was mixed with 10 ml of ether, and the resulting precipitate was filtered off with suction. After drying, 3.48 g (82%) of a white powder remained.
6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In N-methyl-acetamide;
Step E Synthesis of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde as an intermediate Under a nitrogen atmosphere a solution of 2.0 grams (0.013 mole) of 6-chlorosalicylaldehyde in 10 mL of dimethylformamide was stirred, and 1.94 grams (0.0141 mole) of potassium carbonate was added. The reaction mixture was then stirred for 10 minutes, and a solution of 2.6 grams (0.013 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared in Steps A-C) in 15 mL of dimethylformamide was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was warmed to 60° C. where it was stirred for 18 hours. The reaction mixture was poured into 150 mL of water, cooled, and the pH was adjusted to 12 with aqueous 50percent sodium hydroxide, with stirring. The mixture was stirred for 15 minutes, and the resultant solid was collected by filtration to yield 1.62 grams of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde. The nmr spectrum was consistent with the proposed structure.
With potassium carbonate; In n-heptane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
EXAMPLE 6 Preparation of (S)-methyl-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate (Compound II; R'=ethyl, R=methoxy) To a stirred solution of (S)-methyl-2-hydroxy-3-methoxy-3,3-diphenylpropionate (compound IV;50 gms/0.174 moles) and potassium carbonate (26.36 gms/0.191 moles) in DMF (500 ml) was added 4,6-Dimethoxy-2-(methyl sulfonyl)pyrimidine (compound III; R=methoxy) (41.42 gms/0.191 moles) in a dry flask under nitrogen at 25-30 C. The reaction mass was heated to 90-92 C. and further stirred for 1.5 hour. The reaction mass was charged with ethyl acetate (1.5 lit).The organic layer was washed with 2N citric acid (500 ml) followed by water and treated with charcoal. The clear filtrate was distilled completely under vacuum. The residue was stirred with n-heptane (200 ml), filtered, washed with n-heptane (120 ml) and dried to obtain 56 gms of compound (II). The compound (II) was dissolved in acetonitrile (1.12 lit) and isolated in water (2.8 lit). The solid was isolated by filtration and dried to obtain 49 gms of compound (II). Efficiency: 66.10% Purity by HPLC:99.1% Chiral purity: 99.4%
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