Formic Acid → 3-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

HRID 1022479Notes

Reaction equation

HRID 1022479 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][CH2:21][CH2:20]1)[C:14](=[O:25])[N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[C:12]2=[O:37])C1C=CC=CC=1.C(O)=O>CCOC(C)=O>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[O:33][CH3:34])[CH2:26][N:13]1[C:12](=[O:37])[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][CH2:23][CH2:24]2)[C:14]1=[O:25]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 667327516-(benzyloxy)-3-(3,4-dimethoxybenzyl)-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

Product 1

HCID 497642813-(3,4-dimethoxybenzyl)-6-hydroxy-1-(tetrahydro-2H-thiopyran-4-yl)quinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.200 g of the compound obtained in Step 3.2, and 1.22 g of formic acid is irradiated in a microwave field for 2 minutes at 180° C. The reaction mixture is taken up in EtOAc and then evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a CH2Cl2/MeOH mixture from (100/0, v/v) to (97/3, v/v) to give the expected product.

Workup

  1. customis irradiated in a microwave field for 2 minutes at 180° C
  2. customevaporated under reduced pressure
  3. customThe residue is chromatographed on silica gel
  4. washeluting with a CH2Cl2/MeOH mixture from (100/0

Sources & evidence

ORD record
ord-8511f13a9f0b4475ae6e4eadea32894b
Source dataset
uspto-grants-2014_05
Patent number
US08722659B2

Reaction notes

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