盐酸 → 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-morpholinophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 401034笔记

反应方程式

HRID 401034 反应方程式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[C:32]=1[OH:33])[CH:28]=O)[CH3:23].[NH2:37][C:38]([NH2:40])=[O:39].Cl>CCO>[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([CH:28]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:8][CH:9]=3)[NH:40][C:38](=[O:39])[NH:37]2)[CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[C:32]=1[OH:33])[CH3:23]

参与物

6

反应物 4

HCID 313盐酸HCID 1176聚脲HCID 2696961-[4-(Morpholin-4-yl)phenyl]-2-phenylethanone2 次HCID 5848783-乙氧基-4-羟基-5-硝基苯甲醛

产物 1

HCID 569616134-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(4-morpholinophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-one收率 13%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

A mixture of 1-(4-morpholinophenyl)-2-phenylethanone (Intermediate 25) (280 mg, 1.00 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (175 mg, 0.83 mmol), urea (179 mg, 2.99 mmol), and concentrated HCl solution (0.07 mL, 0.83 mmol) in EtOH (5 mL) was refluxed for 48 h. The mixture was evaporated in vacuo, and the residue was purified by preparative HPLC to give Compound 56 (55.29 mg, yield 13%) as a solid. 1H NMR (CD3OD 300 MHz): δ 7.62 (d, J=2.1 Hz, 1H), 7.20-7.15 (m, 3H), 7.10-7.04 (m, 3H), 6.92-6.85 (m, 4H), 5.30 (s, 1H), 4.12-4.02 (m, 2H), 3.81 (t, J=4.8 Hz, 4H), 3.15 (t, J=4.8 Hz, 4H), 1.41 (t, J=6.9 Hz, 3H); MS (ESI): m/z 517.0 [M+1]+.

后处理

  1. temperaturewas refluxed for 48 h
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by preparative HPLC

来源与证据

ORD记录
ord-7e06dab3789b41b4baa90af36026fa71
来源数据集
uspto-grants-2014_06
专利号
US08741915B2

反应笔记

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