Water → 2-Chloro-8-methoxy-7-methylquinazoline

HRID 1672481Notes

Reaction equation

HRID 1672481 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([O:14][CH3:15])[C:6]([CH3:13])=[CH:7][CH:8]=2)[N:3]=1.CCN(C(C)C)C(C)C.[H][H].O>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:14][CH3:15])[C:6]([CH3:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 469418442,4-Dichloro-8-methoxy-7-methylquinazolineHCID 178418361HCID 178418361, compound

Product 1

HCID 469418452-Chloro-8-methoxy-7-methylquinazolineYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dichloro-8-methoxy-7-methylquinazoline (43 g, 0.177 mol) in EtOAc (2580 mL) were added DIPEA (22.9 g, 0.177 mol) and Pd/C (8.6 g) in one portion. The reaction mixture was stirred at room temperature for 6 h under 20 psi of hydrogen. Water (800 mL) was added and the mixture was filtered. The filtrate was separated, the organic layer was washed with water (500 mL). The combined aqueous layers were re-extracted with EtOAc (700 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product. The crude product was re-crystallized from EtOAc (64 mL)/petroleum ether (192 mL) to give the title compound (24.9 g, 67.5%) as a white solid.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was separated
  3. washthe organic layer was washed with water (500 mL)
  4. extractionThe combined aqueous layers were re-extracted with EtOAc (700 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude product
  9. customThe crude product was re-crystallized from EtOAc (64 mL)/petroleum ether (192 mL)

Sources & evidence

ORD record
ord-3a5703d4de8e4ab19cd455c1fafa1379
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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