氯化亚砜 → 4,6-Dimethoxypyrimidine-2-carbonyl chloride

HRID 917361

反应方程式

HRID 917361 反应方程式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([OH:13])=O)[N:4]=1.S(Cl)([Cl:16])=O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([Cl:16])=[O:13])[N:4]=1

参与物

5

反应物 2

HCID 24386氯化亚砜2 次HCID 44224834,6-二甲氧基嘧啶-2-羧酸

产物 1

HCID 230202444,6-Dimethoxypyrimidine-2-carbonyl chloride

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺催化剂HCID 1140甲苯溶剂

实验过程

A mixture consisting of 1.1 g (6.0 mmol) of 4,6-dimethoxypyrimidine-2-carboxylic acid, obtained in accordance with a method descibed in the specification of WO 9318012 A1, 1.1 g (9.0 mmol) of thionyl chloride, one drop of N,N-dimethylformamide and 5 ml of toluene was stirred under heating and refluxing for 3 hours. After the reaction, excess thionyl chloride and the solvent were removed under reduced pressure to obtain crystal of 4,6-dimethoxypyrimidine-2-carbonylchloride. In a separate vessel, 0.30 g (2.0 mmol) of 6,6-difluoro-5-methyl-5-hexenole and 0.61 g (3.0 mmol) of 4,6-dimethoxypyrimidine-2-carbonylchloride were dissolved in 10 ml of tetrahydrofuran, followed by the drop-wise addition of 0.40 g (4.0 mmol) of triethylamine at room temperature, followed by stirring at the same temperature for 1 hour. The reaction liquid was then poured in water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:7) to obtain 0.20 g (yield: 21%) of 6,6-difluoro-5-methyl-5-hexenyl 4,6-dimethoxypyrimidine-2-carboxylate.

后处理

  1. customobtained in accordance with a method
  2. temperatureunder heating
  3. temperaturerefluxing for 3 hours
  4. customthe solvent were removed under reduced pressure

来源与证据

ORD记录
ord-ab2ae2e3076e46808b602e641f4e38cc
来源数据集
uspto-grants-2007_09
专利号
US07273878B2

关联笔记

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