Extracurricular laboratory: Synthetic route of 5-(Hydroxymethyl)pyrimidine

According to the analysis of related databases, 25193-95-7, the application of this compound in the production field has become more and more popular.

Reference of 25193-95-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 25193-95-7, name is 5-(Hydroxymethyl)pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Example 27 Synthesis of 3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylmethoxy)benzofuran-2-yl)-2H-pyran-2-one A solution of tributylphosphine in 2 N THF (0.94 ml) and a solution of TMAD (323 mg) in CH2Cl2 (3 ml) were added dropwise to a solution of 4-acetyloxy-3,5-dimethyl-6-(5-hydroxybenzofuran-2-yl)-2H-pyran-2-one (118 mg) and 5-hydroxymethylpyrimidine (202 mg) in THF (30 ml) at 0 C., and the mixture was stirred at room temperature overnight. The reaction solution was cooled on ice, a 1 N lithium hydroxide aqueous solution (5 ml) was added and the mixture was stirred at room temperature for one hour, after which the reaction solution was again cooled on ice, a 1 N hydrochloric acid aqueous solution (5 ml) and AcOEt were added, the organic layer and aqueous layer were separated, and the aqueous layer was further extracted with AcOEt. The organic layers were combined and dried with MgSO4, and then filtered and concentrated. The residue was purified by silica gel column chromatography (AcOEt/MeOH=10/1) to obtain 3,5-dimethyl-4-hydroxy-6-(5-(5-pyrimidinylmethoxy)benzofuran-2-yl)-2H-pyran-2-one. Yield: 35 mg (y. 26%) 1H NMR(delta ppm, DMSO-d6): 1.95(s, 3H), 2.29(s, 3H), 5.24(s, 2H), 7.12 to 7.14(m, 1H), 7.33 to 7.38(m, 2H), 7.61 to 7.63(m, 1H), 8.95(s, 2H), 9.18(s, 1H), 10.91(brs, 1H)

According to the analysis of related databases, 25193-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teijin Limited; Microbial Chemistry Research Foundation; US6589984; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia