Tetrahydrofuran → HCID 12150401, compound

HRID 275730Notes

Reaction equation

Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:23][CH3:24])=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1.[CH2:25]([N:27](CC)CC)C.C(OCC)(=O)C.O1CCCC1>CN1CCCC1=O>[CH3:22][O:21][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:23][CH3:24])[N:3]=[C:2]([NH:27][CH3:25])[N:11]=[C:10]2[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2.50 g of 2-chloro-6,7-dimethoxy-4-(3-nitrophenyl)quinazoline obtained in Production Example 1,4.89 g methylamine hydrochloride and 11.0 g triethylamine were suspended in 25 ml 1-methyl-2-pyrrolidinone and stirred at 130° C. for 18 hours in a sealed tube. Ethyl acetate and tetrahydrofuran were added thereto, and the reaction solution was washed with water 5 times and then with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (hexane:ethyl acetate=1:2). The product was recrystallized from tetrahydrofuran-ethyl acetate to give 1.89 g of the title compound as yellow crystals.

Workup

washthe reaction solution was washed with water 5 times
dry with materialwith brine and dried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe crude product was purified
customseparated by silica gel column chromatography (hexane:ethyl acetate=1:2)
customThe product was recrystallized from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record: ord-1cd8c7108340447786d3b330e00ac02b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352989B1

Reaction notes

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