반응 #994598

반응 방정식

2,2,2-Trifluoroethanol

NaH

2-amino-4-chloro-6-trifluoromethylpyrimidine

→

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

수율 74.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타for preparation
2. 2
   기타the solvent evaporated
3. 3
   기타The resulting residue was partitioned between CH2Cl2 (200 mL) and H2O (200 mL)
4. 4
   건조The organics separated, dried over MgSO4
5. 5
   여과filtered
6. 6
   기타evaporated

실험 절차

2,2,2-Trifluoroethanol (2.2 mL, 30 mmol) was slowly added to a suspension of NaH (1.5 g, 36 mmol, 60% dispersion in mineral oil) in anhydrous THF (50 mL) under an N2 atmosphere. To the resulting mixture was added a solution of 2-amino-4-chloro-6-trifluoromethylpyrimidine (5.0 g, 25 mmol; for preparation see: Giner-Sorolla, A. and Bendich, A. J. Am. Chem. Soc. 1957, 80, 5744 and Gershon, H. et al. J. Het. Chem. 1983, 20, 219) in anhydrous THF (50 mL). The resulting mixture was stirred 18 h at room temperature and the solvent evaporated. The resulting residue was partitioned between CH2Cl2 (200 mL) and H2O (200 mL). The organics separated, dried over MgSO4, filtered and evaporated to afford 2-amino-4-(2,2,2-trifluoroethoxy)-6-trifluoromethyl-pyrimidine as a tan solid (4.9 g, 74% yield): m.p. 108-110° C.; 1H NMR (CDCl3) δ 6.54 (s, 1H), 5.53 (bs, 2H), 4.76 (q, 2H, J=8.2 Hz); GCMS (EI, 70 eV) m/z 261 (M+).

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