Water → HCID 136347601, compound

HRID 2233262Notes

Reaction equation

HRID 2233262 reaction equation
[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15]CC3C=CC=CC=3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][S:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:15])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68679736HCID 68679736, compound

Product 1

HCID 136347601HCID 136347601, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(methylthio)-6-methoxy-7-benzyloxyquinazoline (29.5 g, 0.095 mol) in trifluoroacetic acid (250 ml) was heated at reflux for 3 hours. The mixture was cooled, water was added, and the pH adjusted to pH 5 with sodium hydroxide (2.0 N). The solid was filtered, washed with water and diethyl ether and dried in vacuo. The solid was redissolved in methanol (2000 ml) and water (500 ml), the pH was adjusted to 7 with sodium hydroxyde (2.0 N) and the precipitated solid was collected by suction filtration. Drying in vacuo yielded 4-(methylthio)-6-methoxy-7-hydroxy-quinazoline (19.18 g, 91% yield):

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe solid was filtered
  4. washwashed with water and diethyl ether
  5. customdried in vacuo
  6. dissolutionThe solid was redissolved in methanol (2000 ml)
  7. filtrationthe precipitated solid was collected by suction filtration
  8. customDrying in vacuo

Sources & evidence

ORD record
ord-eb8c7de1963347dead2cf8d9b95899bc
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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