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

HRID 241433

反応式

HRID 241433 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 (40.0 mL). Heat the mixture to reflux, and stir for 24 hours. Concentrate in vacuo. Dissolve the residue in EtOAc (750 mL); and wash sequentially with saturated aqueous NaS2O3 (250 mL), saturated aqueous NaHCO3 (250 mL), and saturated NaCl (350 mL). Crystallize the orange residue from heptanes/EtOAc to give the title product as a white solid (3.29 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).

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. concentrationConcentrate in vacuo
  4. dissolutionDissolve the residue in EtOAc (750 mL)
  5. washand wash sequentially with saturated aqueous NaS2O3 (250 mL), saturated aqueous NaHCO3 (250 mL), and saturated NaCl (350 mL)
  6. customCrystallize the orange residue from heptanes/EtOAc

出典と根拠

ORDレコード
ord-0e2f83dc904c4fa99ffb89a762c8d4f7
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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