반응 #1979291

반응 방정식

NaH

2-amino-4-(trifluoromethyl)-6-(2,2,2-trifluoroethoxy)pyrimidine

4-trifluoromethylphenyl isocyanate

→

102

수율 44.5%

N-(4-trifluoromethylphenyl)-N′-[4-trifluoromethyl-6-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]urea

수율 44.5%

용매

HCl

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGto stir at room temperature
2. 2
   workup.STIRRINGAfter 18 h of stirring the reaction mixture
3. 3
   추출The acidic mixture was extracted with ethyl acetate
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   workup.ADDITIONThe resulting residue was mixed with ethyl acetate (30 mL)
8. 8
   workup.ADDITIONdiluted with hexane (100 mL)
9. 9
   기타to stand at room temperature
10. 10
    여과After 18 h the insoluble material was filtered
11. 11
    기타dried in a vacuum oven (50° C.)

실험 절차

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).

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