Cesium acetate → 2-Acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one

HRID 47850

Reaction equation

HRID 47850 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[NH:7][C:8]([CH2:12]Cl)=[N:9]2)=[CH:4][C:3]=1[CH3:15].[C:16]([O-:19])(=[O:18])[CH3:17].[Cs+]>CN(C=O)C>[C:16]([O:19][CH2:12][C:8]1[NH:7][C:6](=[O:14])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([CH3:15])[CH:4]=2)[N:9]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 5152919Cesium acetateHCID 1354761257-chloro-2-(chloromethyl)-6-methylquinazolin-4(3H)-one

Product 1

HCID 1354321952-Acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one (0.500 g, 2.06 mmol), anhydrous DMF (14 ml) and cesium acetate (1.58 g, 8.24 mmol) was placed in an oil bath preheated to 85° C., then stirred at this temperature for 2 hours and 15 min under argon. The reaction mixture was then allowed to cool to room temperature and the solvent was removed in vacuo. The residue was treated with hexanes (20 ml), collected by filtration, washed with hexanes (20 ml), water, and dried in vacuo over P2O5 (0.476 g, 87%), mp 220-225° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 2.45 (s, 3H, 6-CH3), 4.95 (s, 2H, 2-CH2O), 7.70, 8.06 (2×s, 2H, 5-H and 8-H), 12.44 (s, 1H, N3—H).

Workup

  1. customwas placed in an oil bath
  2. custompreheated to 85° C.
  3. customthe solvent was removed in vacuo
  4. additionThe residue was treated with hexanes (20 ml)
  5. filtrationcollected by filtration
  6. washwashed with hexanes (20 ml), water
  7. dry with materialdried in vacuo over P2O5 (0.476 g, 87%), mp 220-225° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 2.45 (s, 3H, 6-CH3), 4.95 (s, 2H, 2-CH2O), 7.70, 8.06 (2×s, 2H, 5-H and 8-H), 12.44 (s, 1H, N3—H)

Sources & evidence

ORD record
ord-bc4db9a4f67d43ceb7889c8db31e678b
Source dataset
uspto-grants-2004_03
Patent number
US06699861B1

Linked notes

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