Potassium Carbonate → N-{[4'-({5-[2-(ethyloxy)ethyl]-2,4,6-trioxohexahydropyrimidin-5-yl}oxy)biphenyl-3-yl]methyl}-4-oxo-3,4-dihydroquinazoline-2-carboxamide

HRID 606435Notes

Reaction equation

HRID 606435 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][C:16]([C:18]3[NH:27][C:26](=[O:28])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:30]1([CH2:39][CH2:40][O:41][CH2:42][CH3:43])[C:35](=[O:36])[NH:34][C:33](=[O:37])[NH:32][C:31]1=[O:38].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:42]([O:41][CH2:40][CH2:39][C:30]1([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][C:16]([C:18]4[NH:27][C:26](=[O:28])[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[O:17])[CH:9]=3)=[CH:4][CH:3]=2)[C:31](=[O:38])[NH:32][C:33](=[O:37])[NH:34][C:35]1=[O:36])[CH3:43]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 219311235-Bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trioneHCID 136054510N-[(4'-hydroxybiphenyl-3-yl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide

Product 1

HCID 136054495N-{[4'-({5-[2-(ethyloxy)ethyl]-2,4,6-trioxohexahydropyrimidin-5-yl}oxy)biphenyl-3-yl]methyl}-4-oxo-3,4-dihydroquinazoline-2-carboxamideYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-[(4′-hydroxybiphenyl-3-yl)methyl]-4-oxo-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 119 (0.100 g, 0.269 mmol), 5-bromo-5-[2-(ethyloxy)ethyl]pyrimidine-2,4,6(1H,3H,5H)-trione obtained according to the methods described in WO02/34726 and the like (0.075 g, 0.269 mmol) and potassium carbonate (0.186 g, 1.34 mmol) in DMF (5 mL) was stirred at room temperature for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from ethyl acetate-IPE to give the title compound as a white powder (0.078 g, 51%).

Workup

  1. customobtained
  2. washwashed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was crystallized from ethyl acetate-IPE

Sources & evidence

ORD record
ord-edf679857b1047f0a993eb7dc1b0f7f6
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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