Hydrochloric Acid → 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(pyridin-4-yl)-3,4-dihydropyrimidin-2(1H)-one

HRID 401046ノート

反応式

HRID 401046 の反応式
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[NH2:31][C:32]([NH2:34])=[O:33].Cl>CCO>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 110417042-Phenyl-1-(pyridin-4-yl)ethan-1-one2 回

生成物 1

HCID 513485194-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-6-(pyridin-4-yl)-3,4-dihydropyrimidin-2(1H)-one収率 46%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-phenyl-1-(pyridin-4-yl)ethanone (Intermediate 35) (60 mg, 0.30 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (58 mg, 0.28 mmol), urea (50 mg, 0.83 mmol), and concentrated HCl solution (0.02 mL, 0.28 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was evaporated in vacuo and purified by preparative HPLC to give Compound 71 (55.17 mg, yield 46%). 1H NMR (DMSO-d6 400 MHz): δ 10.29 (br, 1H), 8.92 (s, 1H), 8.53 (d, J=5.6 Hz, 2H), 7.61 (s, 1H), 7.41 (d, J=1.6 Hz, 1H), 7.35 (d, J=1.6 Hz, 2H), 7.12-7.09 (m, 4H), 6.89 (d, J=7.6 Hz, 2H), 5.31 (d, J=2.8 Hz, 1H), 4.03 (q, J=7.2 Hz, 2H), 1.32 (t, J=7.2 Hz, 3H); MS (ESI): m/z 433.0 [M+1]+.

後処理

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated in vacuo
  3. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-a68a6d4bd01b448d97f4821106d609b5
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

反応ノート

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