Methanol → HCID 23681333, compound

HRID 2296484Notes

Reaction equation

HRID 2296484 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:24])[CH:18]([CH3:23])[CH:19]([CH3:22])[CH2:20][CH3:21])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:25]([OH:27])=[O:26].CO.[OH-].[Na+:31].CCOCC>CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:24])[CH:18]([CH3:23])[CH:19]([CH3:22])[CH2:20][CH3:21])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:25]([O-:27])=[O:26].[Na+:31]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 13325979690-61-2

Product 1

HCID 23681333HCID 23681333, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (7.3 g) in N,N-dimethylformamide (120 ml) was added methanol (140 ml) under stirring at 50° C. To this solution was added dropwise sodium hydroxide solution (sodium hydroxide 0.79 g in water 2.37 ml and ethanol 15.8 ml) under stirring for 15 minutes at ambient temperature, and was stirred for 30 minutes at ambient temperature. To this solution ether (250 ml) was added and stirred. The precipitated crystals were collected by filtration and washed two times with water and ether, and dried under reduced pressure to give sodium 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-C]-quinazoline-3-carboxylate (1 hydrate) (4.4 g).

Workup

  1. stirringunder stirring for 15 minutes at ambient temperature
  2. stirringwas stirred for 30 minutes at ambient temperature
  3. stirringstirred
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed two times with water and ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a1bf5e648e514e518f34823f9e559d5b
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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