Trifluoroacetic acid → HCID 118036490, compound

Temperature

50 °C

A mixture of (S)-2,5-dichloro-4-((1-methoxypropan-2-yl)oxy)pyrimidine (intermediate 91, 1.26 g, 4.15 mmol) and 4-methoxybenzylamine (0.65 ml, 4.97 mmol) in DMF (7 ml) was heated at 50° C. for 18 h. The reaction mixture was partitioned between aqueous 1M HCl and DCM, extracted with DCM (2×), the combined DCM layers were washed with water, dried over Na2SO4 and evaporated. To the residue was added trifluoroacetic acid (3.93 ml, 51.0 mmol) and the reaction mixture stood at room temperature for 18 h, heated for 5 h at 70° C., stood 3 days at room temperature, heated at 80° C. for 2 days. The reaction mixture was evaporated and purified by a combination of normal and reversed phase chromatography (RP 3) to give the title compound as a colorless oil. (UPLC-MS 7) tR 0.74; ESI-MS 218.1 and 220.1 [M+H]+.

1. customThe reaction mixture was partitioned between aqueous 1M HCl and DCM
2. extractionextracted with DCM (2×)
3. washthe combined DCM layers were washed with water
4. dry with materialdried over Na2SO4
5. customevaporated
6. temperatureheated for 5 h at 70° C.
7. waitstood 3 days at room temperature
8. temperatureheated at 80° C. for 2 days
9. customThe reaction mixture was evaporated
10. custompurified by a combination of normal and reversed phase chromatography (RP 3)

ORD record

ord-f25bad0c558a4f68952e642d804422b9

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266883B2