Potassium Hydroxide → HCID 135860552, compound

HRID 1428816Notes

Reaction equation

HRID 1428816 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([O:22][CH3:23])[CH:17]=3)[N:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C1COCC1>[CH3:23][O:22][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:24][CH3:25])[N:12]=[C:11]([N:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)[NH:20][C:19]2=[O:21]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 1363371581-(6,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 135860552HCID 135860552, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(6,7-dimethoxy-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.28 g, 0.81 mmol), 1M aq. KOH (3.0 mL) and THF (3.0 mL) was stirred for 4 h. The mixture was concentrated to remove the THF and the aqueous residue was acidified to pH 2 with 1M aq. HCl. The resulting precipitate was collected by filtration to provide the titled compound (0.23 g, 89%). MS (ESI): mass calcd. for C14H12N4O5, 316.3; m/z found, 317.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 13.32-12.29 (br m, 2H), 8.90 (s, 1H), 8.22 (s, 1H), 7.47 (s, 1H), 7.19 (s, 1H), 3.93 (s, 3H), 3.89 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the THF
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-8175c1147fa4408cadc13c415b39a78b
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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