p-Toluenesulfonic acid → 3-(4-sec-butylphenyl)-2-(pyrimidin-5-yl)quinazolin-4(3H)-one

HRID 1846339Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[N:21]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[N:23][CH:22]=1.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CC(N(C)C)=O.C(OCC)(=O)C>[CH:13]([C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:1]=[C:27]2[C:25]2[CH:26]=[N:21][CH:22]=[N:23][CH:24]=2)=[CH:8][CH:9]=1)([CH2:15][CH3:16])[CH3:14]

Participants

Conditions

Temperature: 150 °C

Procedure

2-amino-N-(4-sec-butylphenyl)benzamide (0.544 g, 2.03 mmol) and pyrimidine-5-carbaldehyde (0.241 g, 2.23 mmol), NaHSO3 (0.253 g, 2.44 mmol) and p-TsOH (0.039 g, 0.20 mmol) were dissolved in DMA (20 mL) and heated at 150° C. for 18 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), washed with water (2×200 mL), dried (Na2SO4), filtered, and concentrated. Flash chromatograph on silica gel, eluting with 20% ethyl acetate/heptane to 70% ethyl acetate/heptane, afforded the title compound as a white solid (0.280 g, 39%). 1H-NMR (300 MHz, DMSO-6): δ 9.05 (s, 1H), 8.77 (s, 2H), 8.22-8.25 (m, 1H), 7.92-7.98 (m, 1H), 7.83 (d, J=7.7 Hz, 1H), 7.64-7.69 (m, 1H), 7.31-7.35 (m, 2H), 7.18-7.23 (m, 2H), 2.54-2.61 (m, 1H), 1.37-1.58 (m, 2H), 1.15 (d, J=6.9 Hz, 3H), 0.64 (t, J=7.3 Hz, 3H). MS (APCI) m/z: 357 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
washwashed with water (2×200 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
washFlash chromatograph on silica gel, eluting with 20% ethyl acetate/heptane to 70% ethyl acetate/heptane

Sources & evidence

ORD record: ord-32f7c5893eeb46d6a67cabe14bfa8ef6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952021B2

Reaction notes

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