The origin of a common compound about Methyl 2-chloropyrimidine-5-carboxylate

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference of 287714-35-6, 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 287714-35-6, name is Methyl 2-chloropyrimidine-5-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 5 (200 mg, 562.09 umol, 1 eq, HCl) in DMSO (5 mL) was added Cs2CO3 (549.42 mg, 1.69 mmol, 3 eq) and 5A (97.00 mg, 562.09 umol, 1 eq) at 25 C, the reaction was stirred at 15 C for 10 hr. LCMS showed compound 5 was consumed completely and one main peak with desired mass was detected. The reaction mixture was added water (15 mL), filtered and the filtered cake was concentrated under reduced pressure to give a residue. The crude product was used into the next step without further purification. Compound 6 (210 mg, 413.53 umol, 73.57% yield, 89.69% purity) was obtained as a white solid, and checked by HNMR and HPLC. LCMS: RT = 1.421 min, MS cal.: 455.1, [M+H]+ = 456.1. 1H NMR (400MHz, CHLOROFORM-d) d ppm 8.85 (s, 2H), 6.79 – 6.74 (m, 2H), 6.72 – 6.66 (m, 2H), 4.70 (s, 2H), 4.61 (td, J = 4.9, 14.0 Hz, 2H), 3.89 (s, 3H), 3.82 – 3.76 (m, 3H), 3.73 (s, 3H), 3.69 – 3.59 (m, 2H), 2.11 (ddd, J = 4.1, 9.6, 13.6 Hz, 2H), 1.84 – 1.66 (m, 2H). HPLC: RT= 2.725 min. In some embodiments, LCMS and/or HPLC runs for compounds of the present disclosure may use different conditions and different retention times for the same compound may be observed for different runs.

According to the analysis of related databases, 287714-35-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KLEO PHARMACEUTICALS, INC.; BUNIN, Anna; IBEN, Lawrence G.; MANION, Douglas; SPIEGEL, David Adam; WELSCH, Matthew Ernest; (397 pag.)WO2019/136442; (2019); A1;,
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