Cesium carbonate → 2-(1-(6-chloro-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

Temperatur

50 °C

Intermediate 1 (8.2 g, 43.8 mmol), 4,6-dichloro-2-methylpyrimidine 2-1 (8.2 g, 50.4 mmol) and Cs2CO3 (21.4 g, 65.7 mmol) were suspended in DMA (100 mL) and the mixture was stirred at 50° C. for 3 h. The mixture was cooled to rt, diluted with EtOAc (200 mL), and washed sequentially with water, brine, and water (150 mL each). The combined aqueous phase was back extracted with EtOAc (2×100 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated to give a brownish solid. The solid was triturated with a diethyl ether/DCM mixture (95/5) and then filtered and dried under vacuum to give Intermediate 3 as a light brown solid (10.2 g, 74%). MS: m/z=314.2 (M+H).

1. temperatureThe mixture was cooled to rt
2. washwashed sequentially with water, brine, and water (150 mL each)
3. extractionThe combined aqueous phase was back extracted with EtOAc (2×100 mL)
4. dry with materialThe combined organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a brownish solid
8. customThe solid was triturated with a diethyl ether/DCM mixture (95/5)
9. filtrationfiltered
10. customdried under vacuum

ORD-Eintrag

ord-ba894d7a913e4adc86ac85ed7ae624ed

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09365562B2