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

HRID 1796064Notes

Reaction equation

HRID 1796064 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[C:10]([C:12]3[N:16]4[CH:17]=[CH:18][C:19]([C:21]([CH3:31])([O:23][Si](CC)(CC)CC)[CH3:22])=[N:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:8][N:7]=2)=[CH:2]1>CCO.Cl>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]=[C:10]([C:12]3[N:16]4[CH:17]=[CH:18][C:19]([C:21]([OH:23])([CH3:22])[CH3:31])=[N:20][C:15]4=[N:14][CH:13]=3)[CH:9]=[CH:8][N:7]=2)=[CH:2]1

Participants

4

Reactant 1

HCID 695604373-[2-(Furan-3-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-alpha]pyrimidine

Product 1

HCID 98801472-[3-(2-(Furan-3-yl)pyrimidin-4-yl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-olYield 42.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

3-[2-(Furan-3-yl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (203 mg, 0.47 mmol) in EtOH (10 ml) was treated with conc. HCl (15 drops) and the resulting solution was stirred at room temperature for 12 h during which time a precipitate formed. The solid was filtered off and was then partitioned between CH2Cl2 (20 ml) and NaHCO3 solution (20 ml). The organic layer was separated and the aqueous extracted with CH2Cl2 (3×20 ml). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to afford 2-[3-(2-(furan-3-yl)pyrimidin-4-yl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol (64 mg, 42%): 1H NMR (400 MHz, d6-DMSO) δ 10.29 (1H, d, J 7.3), 8.81 (1H, s), 8.77 (1H, d, J 5.4), 8.68 (1H, s), 7.89 (1H, d, J 5.4), 7.87 (1H, s), 7.74 (1H, d, J 7.3), 7.20 (1H, s), 5.61 (1H, s), 1.54 (6H, s); m/z (ES+) 322 (M+H+).

Workup

  1. customformed
  2. filtrationThe solid was filtered off
  3. customwas then partitioned between CH2Cl2 (20 ml) and NaHCO3 solution (20 ml)
  4. customThe organic layer was separated
  5. extractionthe aqueous extracted with CH2Cl2 (3×20 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3d034ecaf514376acf01807a208237c
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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