7-(1-Methyl-1-triethylsilanyloxyethyl)-3-(2-trifluoromethylpyrimidin-4-yl)imidazo[1,2-alpha]pyrimidine → 2-[3-(2-Trifluoromethylpyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

HRID 1796057ノート

反応式

HRID 1796057 の反応式
[CH3:1][C:2]([C:12]1[CH:17]=[CH:16][N:15]2[C:18]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=3)=[CH:19][N:20]=[C:14]2[N:13]=1)([O:4][Si](CC)(CC)CC)[CH3:3]>CCO.Cl>[F:29][C:27]([F:28])([F:30])[C:23]1[N:22]=[C:21]([C:18]2[N:15]3[CH:16]=[CH:17][C:12]([C:2]([OH:4])([CH3:3])[CH3:1])=[N:13][C:14]3=[N:20][CH:19]=2)[CH:26]=[CH:25][N:24]=1

参加物

4

反応物 1

HCID 695604937-(1-Methyl-1-triethylsilanyloxyethyl)-3-(2-trifluoromethylpyrimidin-4-yl)imidazo[1,2-alpha]pyrimidine

生成物 1

HCID 99232202-[3-(2-Trifluoromethylpyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol収率 60%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 702Ethanol溶媒

実験手順

7-(1-Methyl-1-triethylsilanyloxyethyl)-3-(2-trifluoromethylpyrimidin-4-yl)imidazo[1,2-α]pyrimidine (136 mg, 0.31 mmol) in EtOH (5 ml) was treated with conc. HCl (5 drops) and the mixture stirred at room temperature for 16 h. The resulting mixture was concentrated under reduced pressure and then NaHCO3 solution (20 ml) added. The organics were extracted with CH2Cl2 (3×20 ml) and concentrated under reduced pressure while dry loading onto MgSO4. The residue was purified by column chromatography on silica using 5% MeOH/CH2Cl2 as the eluent to afford 2-[3-(2-trifluoromethylpyrimidin-4-yl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol (60 mg, 60%): 1H NMR (400 MHz, d6-DMSO) δ 9.97 (1H, d, J 7.4), 9.00 (1H, d, J 5.6), 8.97 (1H, s), 8.35 (1H, d, J 5.6), 7.73 (1H, d, J 7.4), 1.53 (6H, s); m/z (ES+) 324 (M+H+).

後処理

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. additionNaHCO3 solution (20 ml) added
  3. extractionThe organics were extracted with CH2Cl2 (3×20 ml)
  4. concentrationconcentrated under reduced pressure
  5. customwhile dry loading onto MgSO4
  6. customThe residue was purified by column chromatography on silica using 5% MeOH/CH2Cl2 as the eluent

出典と根拠

ORDレコード
ord-0c894e5fe6564ed69056fde2823609d2
出典データセット
uspto-grants-2006_04
特許番号
US07030128B2

反応ノート

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