Acetic Acid → HCID 135815317, compound

HRID 1975977Notes

Reaction equation

HRID 1975977 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].[OH-].[K+].[C:15](O)(=O)[CH3:16]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:6]1[CH:16]=[CH:15][CH:3]=[C:4]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][NH:6][C:5]3=[O:12])[CH:5]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 1354016666-Iodoquinazolin-4-one

Product 1

HCID 135815317HCID 135815317, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-Iodo-3H-quinazolin-4-one (4.0 gm, 14.7 mmol), 3-diethylborate pyridine (1.72 gm, 11.75), potassium hydroxide (2.63 gm, 46.95 mmol), tetrabutyl ammonium iodide (2.16 gm, 5.87 mmol) and tetrakis[triphenyl-phosphine] palladium (680 mg, 0.586 mmol) were combined in 70 mL of anhydrous THF and refluxed for 24 hours. The reaction was neutralized with 1.83 mL of acetic acid and filtered product off as a black precipitate. The precipitate was washed with water and THF and then chromatographed on silica gel using 1% pyridine/5% MeCH/CH2Cl2. 1.29 gm (39%) of a pale yellow solid product was obtained.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationfiltered product off as a black precipitate
  3. washThe precipitate was washed with water and THF
  4. customchromatographed on silica gel using 1% pyridine/5% MeCH/CH2Cl2

Sources & evidence

ORD record
ord-816e17165c934a6b903ecc22f364b58c
Source dataset
uspto-grants-2001_05
Patent number
US06225318B1

Reaction notes

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