(2-Chloropyrimidin-5-yl)methanol

(2-Chloropyrimidin-5-yl)methanol is used as an organic synthesis intermediate or starting material in the preparation of active pharmaceutical small molecules, such as Energy Coupling Factor (ECF) transporter inhibitors (compounds used to treat bacterial infections) and androgen receptor (AR) inhibitors (bicyclic compounds).

Starting with (2-chloropyrimidin-5-yl)methanol, the alcohol group was protected with a silyl group, yielding compound 17 (TMPMg.LiCl) in 95 % yield. The chloropyrimidine ring was iodinated using a modified Knochel method, ultimately yielding the iodide 16 [5-(((tert-butyldimethylsilyl)oxy)methyl)-2-chloro-4-iodopyrimidine] in a yield as high as 88 %[1].

[1] Pawluczyk, J. M., Kempson, J., Mathur, A. (2020). Route evaluation and development of a practical synthesis of methyl (S)-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-7-carboxylate. Tetrahedron, 76 49, Article 131624. https://doi.org/10.1016/j.tet.2020.131624