反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:22]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([O:28][C:24]3[C:22]4[N:23]=[C:19]([NH2:18])[S:20][C:21]=4[CH:27]=[CH:26][CH:25]=3)[CH:7]=2)=[CH:9][CH:10]=1参加物
反応条件
- 温度
- 80 °C
実験手順
To a solution of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), ((0.13 g, 0.5 mmol) and 2-amino-4-hydroxybenzothiazole (83 mg, 0.5 mmol, Astatech) in DMF (1 mL) was added potassium carbonate (0.14 g, 1 mmol) and the mixture was heated at 80° C. for 16 h with sirring. The reaction mixture was allowed to cool to room temperature and partitioned between EtOAc and brine. The layers were separated and the aq. layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered and concentrated under vacuum. Purification of the residue by silica gel chromatography (2:1 hexanes:EtOAc) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 389 (M+1). Mp: 232.0–233.5° C. Anal. Calcd for C18H11F3N4OS: C, 55.67; H, 2.85; N, 14.43; S, 8.26. Found: C, 55.52; H, 3.08; N, 14.23; S, 8.36.
後処理
- temperatureto cool to room temperature
- custompartitioned between EtOAc and brine
- customThe layers were separated
- extractionthe aq. layer was extracted with EtOAc
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customPurification of the residue by silica gel chromatography (2:1 hexanes:EtOAc)
出典と根拠
- ORDレコード
- ord-106dcc77b787488a9421b978c6e865ee
- 出典データセット
- uspto-grants-2006_12
- 特許番号
- US07144888B2
関連ノート
読み込み中…