Development of a Scalable Route for a Highly Polar Heterocyclic Aminocyclopropyl Building Block was written by Schafer, Gabriel;Ahmetovic, Muhamed;Fleischer, Tony;Abele, Stefan. And the article was included in Organic Process Research & Development in 2020.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide This article mentions the following:
A robust and scalable route toward key heterocyclic building block 1-(pyrimidin-2-yl)cyclopropan-1-amine hydrochloride from cyclopropanated starting material 1-amino-1-cyclopropanecarbonitrile hydrochloride was successfully developed. The key to success was the construction of a pyrimidine ring via cyclization from an amidine intermediate and a bench-stable 2-chloro vinamidinium hexafluorophosphate salt. The cyclization was performed under mild conditions, and the resulting 4-chloropyrimidine derivative was isolated in high yield and purity. The final hydrogenation was intensively optimized: A combination of Pd(OH)2/C as a catalyst and NaOMe as a base at 1 bar H2 pressure in MeOH simultaneously cleaved the Cbz group and dechlorinated the pyrimidine ring while at the same time suppressing the over-reduction of the pyrimidine ring to below 1.0%. After acidification with HCl, followed by removal of the catalyst and NaCl by filtration, the final product was isolated in high yield and purity as a bench-stable off-white solid. The overall yield of the five-step sequence was 57%. In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide).
1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. It is also used in the manufacturing of dyes such as thioindigo.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem