N-Methylbenzylamine → HCID 59160726, compound

To a suspension of 2,4-dichloro-5-fluoropyrimidine (0.30 g, 1.80 mmol) in dioxane (3.6 mL) were added N-ethyl-N-isopropylpropan-2-amine (0.23 g, 1.80 mmol) and N-methyl-1-phenylmethanamine (0.24 g, 1.98 mmol), and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (15 mL) and the resulting solution was washed with H2O (2×5 mL). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to a light yellow oil which was purified by normal phase chromatography (40 g SiO2; gradient, EtOAc/hexanes) to give a colorless oil which solidified upon cooling. The solid was dried under high vacuum at 23° C. for 16 h to give N-benzyl-2-chloro-5-fluoro-N-methylpyrimidin-4-amine (0.34 g, 76%) as a white solid: mp 47-49° C.; 1H NMR (300 MHz, CDCl3) δ 8.18 (d, J=6.4, 1H), 7.43-7.23 (m, 5H), 4.82 (s, 2H), 3.17 (d, J=3.3, 3H); EIMS m/z 251 (M)+.

1. washthe resulting solution was washed with H2O (2×5 mL)
2. dry with materialThe organic phase was dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo to a light yellow oil which
5. customwas purified by normal phase chromatography (40 g SiO2; gradient, EtOAc/hexanes)
6. customto give a colorless oil which
7. temperatureupon cooling
8. customThe solid was dried under high vacuum at 23° C. for 16 h

ORD record

ord-be46bb7b32a348929cb52744d3b7213b

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318758B2