(1,1'-Biphenyl)-2-ol → HCID 57654527, compound

HRID 1661825Notes

Reaction equation

HRID 1661825 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[CH:5]2.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:13].C1(C2C=CC=CC=2)C(O)=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C1COCC1.[Cu](I)I>[CH2:12]([O:14][C:15](=[O:22])[CH:16]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[CH:5]2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:13]

Participants

8

Reactant 5

HCID 7017(1,1'-Biphenyl)-2-olHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 534359536-Iodoquinazoline

Product 1

HCID 57654527HCID 57654527, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-iodo-quinazoline (0.500 g, 1.95 mmol), malonic acid diethyl ester (0.93 g, 5.81 mmol), copper iodide (0.019 g, 0.097 mmol), biphenyl-2-ol (0.033 g, 0.195 mmol) and cesium carbonate (0.953 g, 2.93 mmol) in THF (5 mL) was heated to 70° C. in a sealed tube for 24 hours. The solution was then cooled to room temperature, saturated ammonium chloride 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 0.39 g (80%) of 2-quinazolin-6-yl-malonic acid diethyl ester. 1H NMR (400 MHz, CDCl3) δ 9.37 (bs, 2H), 7.96 (m, 3H), 4.78 (s, 1H), 4.18 (m, 4H), 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-22b81e3fffbe4904906aad71a3e77c1f
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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