Sodium Iodide → HCID 58507994, compound

Temperature

150 °C

2-Amino-4,6-dimethylpyridine (50 g), bis(2-chloroethyl)ether (57.5 mL), sodium iodide (6.13 g) and triethylamine (137 mL) were mixed in dry N,N-dimethylformamide (1 L) under argon and heated to 150° C. for 16 hours. Water/brine/saturated aqueous sodium bicarbonate (2:1:1, 750 mL) were added to the cooled reaction mixture and it was extracted with ethyl acetate (5×200 mL). The combined organic phases were concentrated in vacuo to app. 500 mL. Water (500 mL) and concentrated aqueous hydrochloric acid (35 mL) were added, the phases separated and the aqueous phase washed with ethyl acetate (200 mL). The aqueous phase was made basic with the addition of concentrated aqueous sodium hydroxide (50 mL) and extracted with isopropyl acetate (5×200 mL). The organic phases was dried over magnesium sulfate and concentrated in vacuo to furnish 44.0 g (56% yield) of the title compound as a black oil. The crude product was used without further purification. GC-MS (m/z) 192 (M+); tR=5.60. 1H NMR (500 MHz, DMSO-d6): 2.08 (s, 3H), 2.26 (s, 3H), 3.39 (m, 4H), 3.68 (m, 4H), 6.05 (s, 1H), 6.44 (s, 1H).

1. extractionwas extracted with ethyl acetate (5×200 mL)
2. concentrationThe combined organic phases were concentrated in vacuo
3. additionWater (500 mL) and concentrated aqueous hydrochloric acid (35 mL) were added
4. customthe phases separated
5. washthe aqueous phase washed with ethyl acetate (200 mL)
6. additionThe aqueous phase was made basic with the addition of concentrated aqueous sodium hydroxide (50 mL)
7. extractionextracted with isopropyl acetate (5×200 mL)
8. dry with materialThe organic phases was dried over magnesium sulfate
9. concentrationconcentrated in vacuo

ORD record

ord-20b1226a994140328e6bf6fe59406502

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812020B2