1,3-Benzenediol, 4-methyl- → HCID 21260287, compound

HRID 634645Notes

Reaction equation

[OH-].[K+].Cl[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]=[CH:6][N:5]=1.[OH:18][C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=1[CH3:26]>O>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][C:10]=1[O:16][CH3:17])[N:7]=[CH:6][N:5]=[C:4]2[O:25][C:23]1[CH:22]=[CH:21][C:20]([CH3:26])=[C:19]([OH:18])[CH:24]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Solid potassium hydroxide (71 mg, 1.2 mmol) and then 4-chloro-6,7-dimethoxyquinazoline (0.25 g, 1.1 mmol), (prepared as described for the starting material in Example 1), were added to a melt of 2,4-dihydroxytoluene (0.6 g, 4.8 mmol) at 140° C. The mixture was stirred at 140° C. for 15 minutes, then allowed to cool. The mixture was diluted with water, and acidified to pH4 then extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The crude product was first purified by flash chromatography eluting with petroleum ether/ethyl acetate (1/9) and then by absorption HPLC eluting with trichloromethane/acetonitrile (85/15) to give 6,7-dimethoxy-4-(3-hydroxy-4-methylphenoxy)quinazoline (116 mg, 34%).

Workup

temperatureto cool
extractionthen extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe crude product was first purified by flash chromatography
washeluting with petroleum ether/ethyl acetate (1/9)
customby absorption HPLC
washeluting with trichloromethane/acetonitrile (85/15)

Sources & evidence

ORD record: ord-b0b6371b3706497e9afb7186e081fdb0
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Reaction notes

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