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

HRID 2178011

反応式

HRID 2178011 の反応式
[CH:1]1([C:6](=O)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[NH2:30][C:31]([NH2:33])=[O:32].Cl>C(O)C>[CH:1]1([C:6]2[NH:33][C:31](=[O:32])[NH:30][CH:21]([C:20]3[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]([OH:26])=[C:18]([O:17][CH2:15][CH3:16])[CH:19]=3)[C:7]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 103976021-Cyclopentyl-2-phenylethan-1-one2 回

生成物 1

HCID 513471876-cyclopentyl-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one収率 3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 1-cyclopentyl-2-phenylethanone (Intermediate 91) (1.6 mmol, 300 mg), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (1.91 mmol, 404 mg), and urea (4.8 mmol, 288 mg) in anhydrous ethanol (5 mL) was added concentrated HCl (0.2 mL), the above mixture was refluxed for 13 hours. The reaction mixture was concentrated and the residue was purified by column chromatography, followed by preparative HPLC to afford the product Compound 172 as yellow solid (20 mg, yield: 2.96%). 1H NMR (DMSO 400 MHz): δ 10.23 (s, 1H), 8.25 (s, 1H), 6.98-7.33 (m, 8H), 5.00 (d, J=2.4 Hz, 1H), 3.94-4.04 (m, 2H), 2.65-2.69 (t, J=9.2 Hz, 1H), 1.24-1.79 (m, 11H); MS (ESI): m/z 424.1 [M+1]+.

後処理

  1. temperaturethe above mixture was refluxed for 13 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-359d41d7841d49bd83851e81b2460056
出典データセット
uspto-grants-2015_06
特許番号
US09067893B2

関連ノート

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