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 1796064ノート

反応式

HRID 1796064 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-c3d034ecaf514376acf01807a208237c
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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