Hydrochloric Acid → 4,5-Pyrimidinediamine, 6-chloro-

Iron dust (1000 g, 17.9 mol) was added to a solution of the crude 6-chloro-5-nitropyrimidin-4-amine (500 g, 2.87 mol) in ethanol (5000 mL) and water (1000 mL). A catalytic amount of concentrated hydrochloric acid (10 mL) was slowly added to the reaction mixture over a period of 20 minutes. During the course of the addition the reaction temperature was observed to increase to 85° C. without external heating and the reaction mixture's color changed from yellow-brown to dark red. After the reaction mixture had cooled down to a temperature of 50° C., the slurry was filtered through a Celite pad, which was then washed with ethanol (3×250 mL). The resulting filtrate was concentrated under reduced pressure to give a yellow solid. This solid was then washed with hexane and dried under reduced pressure to give the title compound as a brown solid. (253 g, overall yield over two steps: 37.1% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.61 (s, 1H), 6.71 (broad s, 2H), 4.94 (broad s, 2H). MS (EI) for C4H5ClN4: 145 (MH+).

1. additionDuring the course of the addition the reaction temperature
2. temperaturewithout external heating
3. temperatureAfter the reaction mixture had cooled down to a temperature of 50° C.
4. filtrationthe slurry was filtered through a Celite pad, which
5. washwas then washed with ethanol (3×250 mL)
6. concentrationThe resulting filtrate was concentrated under reduced pressure
7. customto give a yellow solid
8. washThis solid was then washed with hexane
9. customdried under reduced pressure

ORDレコード

ord-26cec5f7ec424ce5a1cf0c6f49ed6791

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09346807B2