Hydrochloric Acid → 5-Amino-2-methylthio4-(3-methoxyphenyl)-quinazoline-6-carboxylic acid

HRID 1766084Notes

Reaction equation

HRID 1766084 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2.[OH-].[K+].Cl>O1CCOCC1.O>[NH2:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21109094Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylate

Product 1

HCID 211090815-Amino-2-methylthio4-(3-methoxyphenyl)-quinazoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-quinazoline-6-carboxylate (example 25d, 490 mg) was dissolved in 15 ml 1,4-dioxane and a 2 M aqueous KOH solution (3 ml) was added. The mixture was heated at reflux for 5 h and at 70° C. for 76 h. The mixture was cooled to room temperature and a 0.5 M HCl-solution in water was added. The mixture was extracted with CH2Cl2 (2×50 ml), the combined organic layers were dried (MgSO4) and concentrated under reduced pressure to yield the crude title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with CH2Cl2 (2×50 ml)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-299330a0b7624e589315e2af45e48e99
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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