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

HRID 2177895Notes

Reaction equation

HRID 2177895 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH: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>[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:40][C:38](=[O:39])[NH:37][CH:28]([C:27]3[CH:30]=[C:31]([N+:34]([O-:36])=[O:35])[C:32]([OH:33])=[C:25]([O:24][CH2:22][CH3:23])[CH:26]=3)[C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 748171-(1,1'-Biphenyl)-4-yl-2-phenylethan-1-one2×HCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 513479336-(biphenyl-4-yl)-4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5-phenyl-3,4-dihydropyrimidin-2(1H)-oneYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(biphenyl-4-yl)-2-phenylethanone (Intermediate 14) (100 mg, 0.37 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (65 mg, 0.31 mmol), urea (66 mg, 1.1 mmol), and concentrated HCl solution (0.03 mL, 0.37 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was evaporated in vacuo, and purified by preparative HPLC to give Compound 34 (22.52 mg, yield 14%). 1H NMR (DMSO-d6 300 MHz): δ 10.33 (s, 1H), 8.79 (s, 1H), 7.66 (d, J=8.4 Hz, 2H), 7.61-7.58 (m, 3H), 7.47-7.43 (m, 3H), 7.37 (d, J=6.9 Hz, 1H), 7.30 (d, J=8.4 Hz, 2H), 7.22 (s, 1H), 7.09-7.02 (m, 3H), 6.89 (d, J=7.8 Hz, 2H), 5.21 (d, J=2.7 Hz, 1H), 4.06 (q, J=3.6 Hz, 2H), 1.34 (t, J=6.9 Hz, 3H); MS (ESI): m/z 508.1 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-d5a608db5ffd437d96399adaa59f0d01
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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