2-Aminopyrimidine → 2-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

HRID 241455

反応式

HRID 241455 の反応式
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CCO>[CH3:15][C:2]1[N:16]=[C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 79782-AminopyrimidineHCID 104238192-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

生成物 1

HCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine収率 46.85%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Dissolve 2-bromo-1-[4-(trifluoromethyl)phenyl]propan-1-one (7.120 g, 25.332 mmol), and 2-aminopyrimidine (5.464 g, 55.729 mmol) in EtOH (40 mL). Heat the mixture to reflux, and stir for 24 hours. Cool to room temperature, and concentrate under reduced pressure. Dissolve the residue in EtOAc (750 mL). Sequentially wash the organic extracts with a saturated NaS2O3 aqueous solution (250 mL), a saturated NaHCO3 aqueous solution (250 mL), and a saturated NaCl aqueous solution (350 mL). Crystallize the orange residue from heptanes/EtOAc. Collect the title compound as a white solid (3.290 g, 46.85% yield). 1H NMR (399.83 MHz, d6-DMSO) δ 8.84 (dd, J=1.9, 7.0 Hz, 1H), 8.54 (dd, J=2.0, 4.2 Hz, 1H), 8.06-8.04 (m, 2H), 7.83-7.81 (m, 2H), 7.10 (dd, J=4.1, 6.9 Hz, 1H), 2.68 (s, 3H). ES/MS (m/z) 277.99.

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. concentrationconcentrate under reduced pressure
  4. dissolutionDissolve the residue in EtOAc (750 mL)
  5. washSequentially wash the organic extracts with a saturated NaS2O3 aqueous solution (250 mL)
  6. customCrystallize the orange residue from heptanes/EtOAc

出典と根拠

ORDレコード
ord-56429fc81c1e4b6f8d53c99e3a7d1987
出典データセット
uspto-grants-2014_02
特許番号
US08648200B2

関連ノート

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