Tribromoborane-methyl sulfide → 2-Dipropylamino-5-hydroxy-3-methylquinazolin-4(3H)-one

HRID 598074Notes

Reaction equation

HRID 598074 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[C:5]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:17]C)[N:6]=1)[CH2:2][CH3:3].[B-](Br)(Br)(Br)[S+](C)C>ClC(Cl)C>[CH2:19]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:17])[N:6]=1)[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 4181510Tribromoborane-methyl sulfideHCID 67267138HCID 67267138, compound

Product 1

HCID 672670952-Dipropylamino-5-hydroxy-3-methylquinazolin-4(3H)-oneYield 99.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2-dipropylamino-5-methoxy-3-methylquinazolin-4(3H)-one (130 mg, 0.449 mmol) in dichloroethane (2 ml) was added boron tribromide-methyl sulfide complex (1M solution in dichloromethane, 0.899 ml, 0.899 mmol) under nitrogen atmosphere. The mixture was refluxed for 2 h. The reaction was quenched with water and stirred for 10 min at room temperature. The aqueous phase was extracted with ether. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum to afford 123 mg (99%) of the title compound. The residue was used for the next reaction without further purification.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe reaction was quenched with water
  3. extractionThe aqueous phase was extracted with ether
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9f27759245c344d792f12fe5e04db5dc
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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