6-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)-quinazoline-2,4(1H,3H)-dione → 3-(3,4-dimethoxybenzyl)-6-hydroxy-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022511Notes

Reaction equation

HRID 1022511 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH:19]1[CH2:24][CH2:23][S:22](=[O:25])[CH2:21][CH2:20]1)[C:14](=[O:26])[N:13]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1)[C:12]2=[O:38])C1C=CC=CC=1>C(O)=O>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[O:34][CH3:35])[CH2:27][N:13]1[C:12](=[O:38])[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[N:15]([CH:19]2[CH2:20][CH2:21][S:22](=[O:25])[CH2:23][CH2:24]2)[C:14]1=[O:26]

Participants

3

Reactant 1

HCID 667327356-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Product 1

HCID 667322453-(3,4-dimethoxybenzyl)-6-hydroxy-1-(1-oxidotetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dioneYield 93.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 0.57 g of the compound of Step 17.1 and 10 ml of formic acid is irradiated in a microwave field for 3 minutes at 140° C. The reaction mixture is evaporated under reduced pressure. The residue is chromatographed on an RP18 column, eluting with an ACN/water mixture from (10/90, v/v) to (50/50, v/v) to give 0.443 g of the expected product in the form of a mixture of two isomers.

Workup

  1. customis irradiated in a microwave field for 3 minutes at 140° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customThe residue is chromatographed on an RP18 column
  4. washeluting with an ACN/water mixture from (10/90

Sources & evidence

ORD record
ord-ffdfdc7e680e4101b8698f7f9e51c276
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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