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 1796057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796057
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0c894e5fe6564ed69056fde2823609d2
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030128B2

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