6-Methoxy-3-pyridinylamine → 2-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine

Temperature

100 °C

A mixture of 2,4-dichloro-5-iodopyrimidine (274 mg, 0.997 mmol), 5-amino-2-methoxypyridine (0.247 mL, 1.994 mmol), N,N-diisopropylethylamine (0.347 mL, 1.994 mmol) and copper(I) iodide (38 mg, 0.199 mmol) in dioxane (2 mL) was stirred at 100° C. for 3 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as orange oil. The crude product was purified by silica gel chromatography eluting with 40% EtOAc/hexanes to give 2-chloro-5-iodo-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (242 mg, 0.667 mmol, 67.0% yield). 1H NMR (300 MHz, CDCl3) δ 8.44 (s, 1H); 8.28 (d, J=1.90 Hz, 1H); 7.83 (dd, J=8.84, 2.56 Hz, 1H); 7.01 (s, 1H); 6.81 (d, J=8.77 Hz, 1H); 3.96 (s, 3H). m/z (ESI, +ve ion) 362.9 (M+H)+.

1. temperatureThe mixture was cooled down to room temperature
2. extractionextracted with EtOAc (2×30 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (10 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as orange oil
9. customThe crude product was purified by silica gel chromatography
10. washeluting with 40% EtOAc/hexanes

ORD record

ord-298f470d085f4d239438591192789b97

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362241B2