Diisopropylethylamine → (2-Chloro-6-trifluoromethylpyrimidin-4-yl)-methyl-(4-trifluoromethoxyphenyl)-amine

2,4-Dichloro-6-trifluoromethylpyrimidine (XXVII) (1.00 g, 4.6 mmol) was dissolved in dry THF (5 mL). To this solution was added N-methyl-4-trifluoromethoxyaniline (0.88 g, 4.6 mmol) and diisopropylethylamine (0.8 mL, 4.6 mmol). The resulting solution was stirred at room temperature for 18 hrs, then the volatiles were removed in vacuo and the residue was dissolved in CH2Cl2 (50 mL). The CH2Cl2 solution was washed with 2N HCl, dried over MgSO4, filtered and then concentrated in vacuo to give a brown color oil. Purification of the brown oil by chromatography (silica, hexane/EtOAc) afforded the product (XXVIII) as a yellow solid (0.95 g, 56%): 1H NMR (CDCl3) δ 7.42-7.27 (m, 4H), 6.4 (s, 1H), 3.5 (s, 3H); GC/MS m/z (relative intensity) 374 (26), 373 (45), 372 (76), 370 (100).

1. customthe volatiles were removed in vacuo
2. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
3. washThe CH2Cl2 solution was washed with 2N HCl
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give a brown color oil
8. customPurification of the brown oil by chromatography (silica, hexane/EtOAc)

ORD-Eintrag

ord-fa4df1b0d24f41f5b46f6ed40ee3fc15

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08598182B2