Water → 6-Bromo-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one

HRID 1497728Notes

Reaction equation

HRID 1497728 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH:9]([NH:16][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:3]=1.ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:22](=[O:28])[N:16]([CH3:17])[CH:9]2[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 1176000614-Bromo-2-(methylamino-pyridin-2-yl-methyl)-phenylamine

Product 1

HCID 1176006266-Bromo-3-methyl-4-pyridin-2-yl-3,4-dihydro-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 4-Bromo-2-(methylamino-pyridin-2-yl-methyl)-phenylamine (500 mg) in THF (20 mL) is added triphosgene (493 mg, 1.87 mmol), then the mixture is stirred at room temperature for 2 h. TLC showed the reaction is completed. Water (20 mL) is added and the mixture is extracted with EtOAc, the organic layer is dried over Na2SO4 and concentrated to give the desired compound as a crude mixture. This is used in next step with no further purification.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialthe organic layer is dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4ebc16553abd4488950a5bef1ee3aef4
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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