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

HRID 1022513Notes

Reaction equation

HRID 1022513 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:26])(=[O:25])[CH2:21][CH2:20]1)[C:14](=[O:27])[N:13]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1)[C:12]2=[O:39])C1C=CC=CC=1>C(O)=O>[CH3:38][O:37][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][C:32]=1[O:35][CH3:36])[CH2:28][N:13]1[C:12](=[O:39])[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:26])(=[O:25])[CH2:23][CH2:24]2)[C:14]1=[O:27]

Participants

3

Reactant 1

HCID 667328576-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-quinazoline-2,4(1H,3H)-dione

Product 1

HCID 667326983-(3,4-dimethoxybenzyl)-1-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-6-hydroxyquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 0.42 g of the compound obtained in Step 18.1 and 3.66 g of formic acid is irradiated in a microwave field for 10 minutes at 180° C. The reaction mixture is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a DCM/MeOH mixture from (100/0, v/v) to (90/10, v/v), to give the expected product.

Workup

  1. customis irradiated in a microwave field for 10 minutes at 180° C
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customThe residue is chromatographed on silica gel
  4. washeluting with a DCM/MeOH mixture from (100/0

Sources & evidence

ORD record
ord-f0b04f654af142118c1a2b444408bff2
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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