Ammonia → 8-isopropyl-7-methoxyquinazolin-2(1H)-one

HRID 1609796Notes

Reaction equation

N[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([CH:14]([CH3:16])[CH3:15])[C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.N([O-])=[O:18].[Na+].N>F[B-](F)(F)F.[H+]>[CH:14]([C:5]1[C:6]([O:12][CH3:13])=[CH:7][CH:8]=[C:9]2[C:4]=1[NH:3][C:2](=[O:18])[N:11]=[CH:10]2)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-amino-7-methoxy-8-(2-propyl)quinazoline (1.3 g) in tetrafluoroboric acid (50 mL), sodium nitrite solution (2.6 g in 10 mL of water) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 18 hours. The reaction mixture was cooled in an ice bath and neutralized with 30% ammonia solution. The product was extracted with ethyl acetate (3×50 mL), combined organic extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound as an off-white solid (1.2 g, 92.3%). mp 188–190° C. (decom); 1H NMR (CDCl3): δ 1.32 (d, 6H, 2×CH3), 3.44 (m, 1H, CH), 3.97 (s, 3H, OCH3), 6.88 (d, 1H, Ar-H, J=8.8 Hz), 7.59 (d, 1H, Ar-H, 8.8 Hz), 9.0 (s, 1H, Ar-H), 9.1 (brs, 1H, NH).

Workup

temperatureThe reaction mixture was cooled in an ice bath
extractionThe product was extracted with ethyl acetate (3×50 mL)
extractioncombined organic extract
washwas washed with brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-11cf2d9f33f0442086d5b3a46e273d64
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982260B1

Reaction notes

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