Sodium Carbonate → 6-(3,5-Dimethyl-isoxazol-4-yl)-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one

HRID 1497729Notes

Reaction equation

HRID 1497729 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[CH:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[CH3:20][C:21]1[C:25](B(O)O)=[C:24]([CH3:29])[O:23][N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:21]1[C:25]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[N:6]([CH3:13])[CH:5]3[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:24]([CH3:29])[O:23][N:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 1176006266-Bromo-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one

Product 1

HCID 1176000606-(3,5-Dimethyl-isoxazol-4-yl)-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a solution of crude 6-Bromo-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one (600 mg, 0.002 mol) in DME/H2O (12 mL/4 mL) is added 3,5-dimethylisoxazole-4-boronic acid (265 mg, 0.002 mol), Pd(PPh3)4 (77 mg, 0.08 mmol) and Na2CO3 (332 mg, 3.14 mmol). After addition, the mixture is refluxed for 3 h. The mixture is concentrated in vacuum and the residue is purified by preparative HPLC to give the desired product as a yellow solid.

Workup

  1. additionAfter addition
  2. temperaturethe mixture is refluxed for 3 h
  3. concentrationThe mixture is concentrated in vacuum
  4. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-bf3722dea41f4140aa271703f3df41dd
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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