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 1796057Notes

Reaction equation

HRID 1796057 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-0c894e5fe6564ed69056fde2823609d2
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

Loading…