2-Aminopyridine → N-(5-pyrimidinylmethylene)-2-pyridinamine

A solution of 2-aminopyridine (11.314 g, 120.3 mmole) and pyrimidine-5-carboxaldehyde (14.0 g, 129.6 mmole) in chloroform (300 mL) was stirred at room temperature for 15 minutes. The volatiles were then removed under reduced pressure (1 hour at 75° C.) to yield a yellow solid. The crude solid was dissolved in chloroform (300 mL), and the solution was stirred for 15 minutes. The volatiles were then removed under reduced pressure (1 hour at 75° C.) to yield a yellow solid. The crude solid was again dissolved in chloroform (300 mL), the solution was stirred for 15 minutes, and the volatiles were removed under reduced pressure (1 hour at 85° C.) to yield a yellow solid. This solid was dried in a vacuum oven overnight at 80° C. to yield 22.090 g (99.8%) of the title compound. 1H NMR (CDCl3) δ 9.26-9.32 (m, 4H), 8.52 (d, 1H), 7.82 (t, 1H), 7.42 (d, 1H), 7.26 (t, 1H).

1. customThe volatiles were then removed under reduced pressure (1 hour at 75° C.)
2. customto yield a yellow solid
3. customThe volatiles were then removed under reduced pressure (1 hour at 75° C.)
4. customto yield a yellow solid
5. stirringthe solution was stirred for 15 minutes
6. customthe volatiles were removed under reduced pressure (1 hour at 85° C.)
7. customto yield a yellow solid
8. customThis solid was dried in a vacuum oven overnight at 80° C.

ORD record

ord-1cea720a338b4639ae73f96312819504

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895738B2