Citric Acid → HCID 178497329, compound

HRID 1801869Notes

Reaction equation

HRID 1801869 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:13]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=O.[C:44]([OH:56])(=[O:55])CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C.CO>[CH3:13][O:56][C:44]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[OH:1])=[O:55]

Participants

9

Reactant 4

HCID 311Citric AcidHCID 812191,3-Bis(diphenylphosphino)propaneHCID 178418416HCID 178418416, compound2×HCID 178518013HCID 178518013, compound

Product 1

HCID 178497329HCID 178497329, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4-Hydroxy-6-iodoquinazoline (250 mg), a catalytic amount of palladium (II) acetate and 1,3-bis(diphenylphosphino)propane were dissolved in N,N-dimethylformamide (3.8 ml) and methanol (1.5 ml) and 1.5 ml of triethylamine was added. After the interior of a reaction vessel was sufficiently replaced with a carbon monoxide gas, a reaction was performed at 80° C. for 20 hours under the carbon monoxide atmosphere. After completion of the reaction, the reaction mixture was poured into 10% aqueous citric acid, followed by extraction with ethyl acetate. The organic layer was washed with water, and dried over sodium sulfate, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (eluting with ethyl acetate) to obtain 4-hydroxyquinazoline-6-carboxylic acid methyl ester (XII-1, 157 mg) as a brown solid.

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was purified by silica gel column chromatography (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-33fd6747736241a09fe91b688219fc13
Source dataset
uspto-grants-2013_01
Patent number
US08349857B2

Reaction notes

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