Aniline → 2-Aminoquinazoline 6

HRID 1609798Notes

Reaction equation

Cl[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.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[CH:14]([C:5]1[C:6]([O:12][CH3:13])=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:11]=[CH:10]2)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-chloro-7-methoxy-8-(2-propyl)quinazoline (100 mg, 0.42 mmol) and aniline (120 mg, 1.29 mmol) in acetonitrile (3 mL), was heated at 80° C. for 18 hours in a sealed tube. The solvent was removed under reduced pressure, to the residue 5% sodium carbonate solution was added. The product was extracted with ethyl acetate (3×25 mL). The combined organic extract was washed with brine, dried (Na2SO4), and concentrated. The product was purified on a column of silica gel to give the title compound as an off-white solid (95 mg, 76.3%), mp 172–173° C.; 1H NMR (CDCl3): δ 1.46 (d, 6H, 2×CH3), 3.97 (s, 3H, OCH3), 4.33 (m, 1H, CH), 7.0–7.1 (m, 2H, Ar-H), 7.38 (t, 2H, Ar-H, 7.58 (d, 1H, Ar-H), 7.85 m, 2H, Ar-H), 8.93 (s, 1H, Ar-H); MS m/z C18H19N3O 294.21 (M++1); Analysis: Calcd.; C, 73.7; H, 6.53; N, 14.32. Found: C, 73.8; H, 6.83; N, 14.59.

Workup

customThe solvent was removed under reduced pressure, to the residue 5% sodium carbonate solution
additionwas added
extractionThe product was extracted with ethyl acetate (3×25 mL)
extractionThe combined organic extract
washwas washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe product was purified on a column of silica gel

Sources & evidence

ORD record: ord-f1cb0622c36a4539bf67d6e7e331e404
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06982260B1

Reaction notes

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