Ozone → 3-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydro-quinazoline-6-carbaldehyde

HRID 1022506Notes

Reaction equation

HRID 1022506 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:9][N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:21]=C)[CH:17]=2)[N:12]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:11]1=[O:29]>C(Cl)Cl>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH2:9][N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH:21]=[O:1])[CH:17]=2)[N:12]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:11]1=[O:29]

Participants

4

Reactant 2

HCID 24823OzoneHCID 497631873-(3,4-dimethoxybenzyl)-6-ethenyl-1-(tetrahydro-2H-pyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 866647683-(3,4-dimethoxybenzyl)-2,4-dioxo-1-(tetrahydro-2H-pyran-4-yl)-1,2,3,4-tetrahydro-quinazoline-6-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A stream of ozone is passed for 10 minutes through a solution of 1.4 g of the compound obtained in Step 14.1 in 100 ml of DCM cooled to −78° C. The reaction medium is degassed with nitrogen, 40 ml of dimethyl sulfide are added and the resulting mixture is stirred overnight at room temperature. The reaction medium is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/EtOAc mixture from (100/0, v/v) to (60/40, v/v) to give 0.58 g of the expected product.

Workup

  1. customThe reaction medium is degassed with nitrogen, 40 ml of dimethyl sulfide
  2. additionare added
  3. customThe reaction medium is evaporated under reduced pressure
  4. customThe residue is chromatographed on silica gel
  5. washeluting with a DCM/EtOAc mixture from (100/0

Sources & evidence

ORD record
ord-ed483b7064ad4ec6ae4e752786e27131
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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