N,N-dimethyl-5-nitropyridin-2-amine → N2,N2-dimethylpyridine-2,5-diamine

To a solution of 2-dimethylamino-5-nitropyridine (334 mg, 2 mmol) in 100 ml of methanol was added 5% Pd/C (100 mg, 0.94 mmol). The reaction mixture was hydrogenated under 45 psi at room temperature for 2 h, then it was filtered through a layer of celite (2.5 in d×2 in h) and washed with additional methanol (25 ml). The organic filtrate was concentrated to yield 200 mg (73%) of 2-dimethylamino-5-amino-pyridine as dark brown sticky solids. The title compound was prepared from 4-chloro-2-methyl-quinazoline (182.2 mg, 1.02 mmol), 2-dimethylamino-5-amino-pyridine (140 mg, 1.02 mmol) and sodium acetate (98.4 mg, 1.2 mmol) similar to example 20 to give 60 mg (21%) of paint yellow solids. 1H NMR (CDCl3): 8.43 (d, J=2.4 Hz, 1H), 7.95 (dd, J=2.7 Hz, J=9.3 Hz, 1H), 7.84-7.72 (m, 3H), 7.47 (t, J=8.1 Hz, 1H), 7.16 (brs, 1H), 6.61 (d, J=9.0 Hz, 1H), 3.12 (s, 6H), 2.65 (s, 3H).

1. filtrationit was filtered through a layer of celite (2.5 in d×2 in h)
2. washwashed with additional methanol (25 ml)
3. concentrationThe organic filtrate was concentrated

ORD record

ord-b78fb107c2d348b89d9032eacbeb48a3

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989462B2