Potassium Phosphate, Tribasic → HCID 178489278, compound

HRID 1374253Notes

Reaction equation

HRID 1374253 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[OH:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[OH:12]

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27339582-Methoxyphenylboronic acidHCID 178517953HCID 178517953, compound

Product 1

HCID 178489278HCID 178489278, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Preparation D6, Step 2: A mixture of 6-bromoquinazolin-4-ol (227 mg, 1.01 mmol), 2-methoxyphenylboronic acid (307 mg, 2.02 mmol), 2.0 M potassium phosphate (aq) (1.5 mL, 3.0 mmol), and DMF (3 mL) in a 5 mL microwave tube was degassed under vacuum/Ar. A catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube, the mixture was degassed again, the tube was sealed, and the reaction was heated at 150° C. in the microwave for 30 min. The resulting black mixture was filtered, then concentrated in-vacuo. The residue was taken up in 9:1 ethyl acetate/heptane (50 mL), washed with water (3×20 mL), then brine, then dried over sodium sulfate and concentrated in-vacuo. The residue was purified over silica gel, eluting with 1:1 ethyl acetate/heptane, 100% ethyl acetate, then 9:1 ethyl acetate/methanol, to yield 250 mg of 6-(2-methoxyphenyl)quinazolin-4-ol as a white powder. MS (ES+)=253 (M+H+).

Workup

  1. customwas degassed under vacuum/Ar
  2. additionA catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added to the tube
  3. customthe mixture was degassed again
  4. customthe tube was sealed
  5. filtrationThe resulting black mixture was filtered
  6. concentrationconcentrated in-vacuo
  7. washwashed with water (3×20 mL)
  8. dry with materialbrine, then dried over sodium sulfate
  9. concentrationconcentrated in-vacuo
  10. customThe residue was purified over silica gel
  11. washeluting with 1:1 ethyl acetate/heptane, 100% ethyl acetate

Sources & evidence

ORD record
ord-de54cb35804146a5bb2c48f209d4e556
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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