2,4-Dichloro-6,7-dimethoxyquinazoline → 2,4-Dichloro-6,7-dimethoxy-5-nitroquinazoline

HRID 353043

Reaction equation

HRID 353043 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.F[B-](F)(F)F.[O:22]=[N+:23]=[O:24]>C(#N)C>[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[C:8]=2[N+:23]([O-:24])=[O:22])[N:3]=1

Participants

4

Reactant 2

HCID 5203272,4-Dichloro-6,7-dimethoxyquinazolineHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 227070482,4-Dichloro-6,7-dimethoxy-5-nitroquinazolineYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2,4-dichloro-6,7-dimethoxyquinazoline (30.0 g, 0.12 mol) in acetonitrile (550 ml) at 0° C. was added nitronium tetrafluoroborate (25.9 g, 0.19 mol) portionwise over 15 min. The reaction was stirred for 0.75 h and then evaporated under reduced pressure. The resulting solid was suspended in a mixture of saturated aqueous sodium bicarbonate and EtOAc and the solid filtered, dissolved in CH2Cl2, dried over MgSO4 and evaporated to give the subtitle compound as a pale yellow solid (27 g). Further material was obtained by separating the organic layer of the filtrate, washing with H2O (1×), saturated brine (1×), drying over MgSO4 and filtering through a pad of silica. Subsequent evaporation under reduced pressure, trituration with EtOAc and filtration gave the subtitle compound as a pale yellow solid (3.9 g, overall yield 88%). Rf 0.24 (ether/hexane 1/1, v/v).

Workup

  1. customevaporated under reduced pressure
  2. additionThe resulting solid was suspended in a mixture of saturated aqueous sodium bicarbonate and EtOAc
  3. filtrationthe solid filtered
  4. dissolutiondissolved in CH2Cl2
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-1d53f366d6aa40a38022f11709a45a87
Source dataset
uspto-grants-2004_06
Patent number
US06750214B2

Linked notes

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