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 1796064노트

반응식

HRID 1796064 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 702Ethanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-c3d034ecaf514376acf01807a208237c
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030128B2

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