1-Bromo-3-chloropropane → 7-(3-Chloropropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 855709Notes

Reaction equation

HRID 855709 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[OH:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[N:12]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=[N:14]2)=[CH:9][C:8]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:5][CH2:4][CH2:3][CH2:2][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:25])[N:12]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[CH:13]=[N:14]2)=[CH:9][C:8]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 179427567-(3-Chloropropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-chloropropane (0.97 ml, 9.8 mmol) was added to a solution of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.5 g, 8.17 mmol), (prepared as described for the starting material in Example 7), in DMF (40 ml) containing potassium carbonate (2.8 g, 20 mmol). The mixture was stirred overnight at ambient temperature and partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried (MgSO4) and evaporated to give 7-(3-chloropropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (3.10 g, 100%).

Workup

  1. custom(prepared
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-b7564629bbbc4df080f66c77be935bed
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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