Sodium hydride → HCID 57651773, Verbindung

To a suspension of NaH (152 mg, 3.8 mmol, 60% dispersion in mineral oil) in anhydrous THF (2 mL) at room temperature was slowly added a solution of 2-amino-4-(trifluoromethyl)-6-(2,2,2-trifluoroethoxy)pyrimidine (0.50 g, 1.9 mmol) in anhydrous THF (2 mL) and the resulting mixture was stirred 20 min. To the mixture was added 4-trifluoromethylphenyl isocyanate (326 μL, 2.28 mmol) and the resulting mixture was allowed to stir at room temperature. After 18 h of stirring the reaction mixture was diluted with 2 N HCl (30 mL). The acidic mixture was extracted with ethyl acetate. The organics were combined, dried over MgSO4, filtered and concentrated. The resulting residue was mixed with ethyl acetate (30 mL), diluted with hexane (100 mL) and allowed to stand at room temperature. After 18 h the insoluble material was filtered and dried in a vacuum oven (50° C.) to afford 102 as a white solid (379 mg, 44% yield): m.p. 197-199° C.; 1H NMR (DMSO-d6) δ 10.76 (s, 1H), 10.71 (s, 1H), 7.72 (app s, 4H). 7.35 (s, 1H), 5.25-5.16 (q, 2H, J=8.9 Hz); ESI/MS 448 (M+H), 447 (M−H).

1. stirringto stir at room temperature
2. stirringAfter 18 h of stirring the reaction mixture
3. extractionThe acidic mixture was extracted with ethyl acetate
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. additionThe resulting residue was mixed with ethyl acetate (30 mL)
8. additiondiluted with hexane (100 mL)
9. customto stand at room temperature
10. filtrationAfter 18 h the insoluble material was filtered
11. customdried in a vacuum oven (50° C.)

ORD-Eintrag

ord-5c6a144dc7704607bcffd18979ecd20d

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08013154B2