Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-(2-Hydroxy-2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1751892Notes

Reaction equation

O1CCCCC1[O:7][CH:8]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)[CH2:9][O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][N:12]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[OH:7][CH:8]([C:21]1[CH:22]=[CH:23][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][CH:26]=1)[CH2:9][O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][N:12]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-(2-tetrahyropyranyloxy-2-(4-tert-butylphenyl)ethoxy) quinazoline (0.25 g, 0.615 mmol) is dissolved in 5 ml ethanol and pyridinium-p-toluenesulfonate (15.4 mg, 0.061 mmol) is added to it. The solution is heated to 55° C. and stirred at that temperature for 4 hours. The ethanol is removed and the crude is purified by flash chromatography (silica gel; ethyl acetate/hexanes).

Workup

customThe ethanol is removed
customthe crude is purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-b37f8f99918b406f9edd6487db7b91b2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09161997B2

Reaction notes

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