Hydrochloric Acid → HCID 67271495, compound

Temperature

100 °C

To a solution of N-(3-amino-4-methylphenyl)acetamide (5 g, 25 mmol, commercially available) in DMF (5 mL) was added 2-chloro-4-(pyridin-3-yl)-pyrimidine (4 g, 35 mmol, commercially available) and KI (0.5 g, 3 mmol). After stirring at 100° C. overnight, the reaction mixture was cooled to 10° C., quenched with H2O, (100 mL), extracted with CH2Cl2 (2×100 mL) and the combined organic layers were dried (Na2SO4) and concentrated. The residue was dissolved in conc. HCl (10 mL), stirred at 80° C. for 2 h, and then concentrated to yield 6-methyl-N′-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine hydrochloride (4.5 g, 65% yield) as the HCl salt. 1H NMR (300 MHz, CDCl3): δ 7.93-7.96 (m, 2H), 7.50-7.47 (m, 1H), 7.47-7.41 (m, 5H), 7.25-7.27 (m, 2H), 2.21 (s, 3H); MS (ESI) m/e: 277 (M+H+).

1. temperaturethe reaction mixture was cooled to 10° C.
2. customquenched with H2O, (100 mL)
3. extractionextracted with CH2Cl2 (2×100 mL)
4. dry with materialthe combined organic layers were dried (Na2SO4)
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in conc. HCl (10 mL)
7. stirringstirred at 80° C. for 2 h
8. concentrationconcentrated

ORD record

ord-b791538485b843f0903053e015f4bdf7

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163756B2