Hydroxylamine → 4-Methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-amine

HRID 241435ノート

反応式

HRID 241435 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[N:9]=CC=C[N:5]2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.NO>CCO>[CH3:1][C:2]1[N:3]=[C:4]([NH2:9])[NH:5][C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 787HydroxylamineHCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

生成物 1

HCID 1784333994-Methyl-5-[4-(trifluoromethyl)phenyl]-1H-imidazol-2-amine収率 95%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Stir a mixture of 2-methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine (180 g, 649.2 mmol, 1 equiv) in EtOH (1.4 L) and hydroxylamine (159 ml, 2.596 mol, 4 equiv) at an internal temperature of 82° C. for 48 hours. Cool the mixture, and concentrate to dryness. Dilute the residue with DCM (1.5 L), and wash sequentially with water (2×500 ml) and brine (500 ml). Dry the organic phase over MgSO4; filter; collect the filtrate and; and remove the solvent in vacuo to give a yellow gum. Purify the resulting material by flash chromatography on silica gel (2 kg), eluting with a gradient of 4:1:0.02 DCM/MeOH/NH3 to obtain the title compound as a yellow foam (95% yield). MS (m/z) 242 (M+1).

後処理

  1. temperatureCool the mixture
  2. concentrationconcentrate to dryness
  3. additionDilute the residue with DCM (1.5 L)
  4. washwash sequentially with water (2×500 ml) and brine (500 ml)
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. customcollect the filtrate
  8. customand remove the solvent in vacuo
  9. customto give a yellow gum
  10. customPurify the resulting material by flash chromatography on silica gel (2 kg)
  11. washeluting with a gradient of 4:1:0.02 DCM/MeOH/NH3

出典と根拠

ORDレコード
ord-9ed8440d7c3c47dc8cf5013c054f3279
出典データセット
uspto-grants-2014_02
特許番号
US08648200B2

反応ノート

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