反応式
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([I:18])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C([N:21](CC)C(C)C)C.Cl[C:28]1[C:33]([C:34](Cl)=[O:35])=[C:32](Cl)[N:31]=[CH:30][N:29]=1.CCOC(C)=O>C1NC2NC(N)=NC(=O)C=2N2C1CN(C1C=CC(C(N[C@H](C(O)=O)CCC(O)=O)=O)=CC=1)C2.CCCCCCC>[NH2:21][C:28]1[C:33]2[C:34](=[O:35])[N:11]([C:12]3[CH:13]=[CH:14][C:15]([I:18])=[CH:16][CH:17]=3)[CH2:10][CH2:9][O:8][C:32]=2[N:31]=[CH:30][N:29]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To a cooled (ice/water), stirred solution of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-iodoaniline (1.34 g, 2.78 mmol) and diethylisopropylamine (0.7 mL, 4.0 mmol) in MTHF (5 mL) was added 4,6-dichloroprimidine-5-carbonyl chloride (560 mg, 2.65 mmol). After 5 minutes, the cooling bath was removed and the slurry was stirred for 5 hours. Aqueous hydrochloric acid (1N, 5 mL) was added and the mixture was allowed to stand for 72 hours. The layers were separated and the aqueous layer was washed with MTHF (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo to afford an oil. Chromatography (40 g silica gel column, 20-100% EtOAc:heptane) afforded the title compound, 542 mg. 1H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 7.62 (d, 2H), 7.17 (d, 2H), 4.07 (t, 2H), 3.91 (q, 2H). m/z=438.0 (M+1).
後処理
- customthe cooling bath was removed
- additionAqueous hydrochloric acid (1N, 5 mL) was added
- waitto stand for 72 hours
- customThe layers were separated
- washthe aqueous layer was washed with MTHF (2×)
- washThe combined organic layers were washed with saturated aqueous sodium bicarbonate, saturated aqueous brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customto afford an oil
出典と根拠
- ORDレコード
- ord-76521802846e4ca3acc1f88eb4436c47
- 出典データセット
- uspto-grants-2010_05
- 特許番号
- US07718645B2
関連ノート
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