Sodium borohydride → 4-[N-(2-pyrimidinyl)aminomethyl]aniline

In THF (20 ml) and methanol (20 ml) was dissolved N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amine (921 mg, 4.00 mmol), and to the mixture were added at 0° C. nickel bromide (137 mg) and sodium boro hydride(955 mg). The mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. To the residue were added ethyl acetate, THF and water, and the insoluble materials were filtered off. The aqueous layer was extracted with ethyl acetate-THF, and the organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/1), and the desired fraction was concentrated under reduced pressure. To the residue was added diethylether, and the insoluble materials were filtered, which were washed with diethylether and dried under reduced pressure to give 4-[N-(2-pyrimidinyl)aminomethyl]aniline (208 mg, 1.04 mmol, 26%).

1. concentrationconcentrated under reduced pressure
2. additionTo the residue were added ethyl acetate, THF and water
3. filtrationthe insoluble materials were filtered off
4. extractionThe aqueous layer was extracted with ethyl acetate-THF
5. dry with materialthe organic layer was dried with anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified with column chromatography (silica gel 30 g, ethyl acetate/hexane=1/1)
8. concentrationthe desired fraction was concentrated under reduced pressure
9. additionTo the residue was added diethylether
10. filtrationthe insoluble materials were filtered
11. washwhich were washed with diethylether
12. customdried under reduced pressure

ORD record

ord-88b0719438e8436eb2d36d81779b1e3e

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06172061B2