(1,1'-Biphenyl)-2-ol → HCID 57654588, compound

HRID 1921644Notes

Reaction equation

HRID 1921644 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:5]2=[O:21].[CH2:22]([O:24][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:23].C1(C2C=CC=CC=2)C(O)=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>C1COCC1.[Cu](I)I>[CH2:22]([O:24][C:25](=[O:32])[CH:26]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:5]2=[O:21])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:23]

Participants

8

Reactant 5

HCID 7017(1,1'-Biphenyl)-2-olHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 57654506HCID 57654506, compound

Product 1

HCID 57654588HCID 57654588, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-iodo-3-(4-methoxy-benzyl)-3H-quinazolin-4-one (0.69 g, 1.75 mmol), malonic acid diethyl ester (0.56 g, 3.49 mmol), copper iodide (0.016 g, 0.090 mmol), biphenyl-2-ol (0.029 g, 0.175 mmol) and cesium carbonate (0.86 g, 2.63 mmol) in THF (10 mL) was heated to 70° C. in a sealed tube for 24 hours. The solution was then cooled to room temperature, saturated sodium bicarbonate was added and the crude product was extracted from ethyl acetate. The product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 0.51 g (69%) of 2-[3-(4-methoxy-benzyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-malonic acid diethyl ester. 1H NMR (400 MHz, CDCl3) δ 8.21 (m, 1H), 8.05 (s, 1H), 7.80 (dd, 1H, J=2.0, 8.4 Hz), 7.62 (d, 1H, J=8.4 Hz), 7.22 (d, 2H, J=8.8 Hz), 6.78 (d, 2H, J=8.8 Hz), 5.05 (s, 2H), 4.69 (s, 1H), 4.15 (m, 4H), 3.70 (s, 3H), 1.19 (m, 6H).

Workup

  1. extractionthe crude product was extracted from ethyl acetate
  2. customThe product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-af0e0e789cd043b1a56e8650bc244f9a
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

Loading…