5-Methylfurfural → 7,9-dimethyl-6-(5-methylfuran-2-yl)-11-phenyl-5,6-dihydropyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione

HRID 1912357Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:23]2[C:18]([N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22]2=[O:31])=[CH:17]1>C(O)C>[CH3:1][C:2]1[O:6][C:5]([CH:7]2[NH:9][C:10]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:16]3[C:17]2=[C:18]2[N:19]([CH3:34])[C:20](=[O:33])[N:21]([CH3:32])[C:22](=[O:31])[C:23]2=[C:24]3[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 5-methylfuran-2-carbaldehyde (32 mg, 29 μl, 0.29 mmol), compound 6 (101 mg, 0.29 mmol), and ethanol (1 mL) were heated in a microwave reactor at 170° C. for 10 min. A white product was isolated, washed and recrystallized from ethanol to afford 51 mg of 7 (42% yield); m.p.>300° C.; 1H NMR (DMSO-d6): δ 7.41 (broad m, 4H), 6.95 (d, 2H, J=8.42 Hz), 6.90-6.83 (m, 2H), 6.29 (d, 2H, J=2.93 Hz), 6.08 (d, 1H, J=2.19 Hz), 5.80 (d, 1H, J=2.93 Hz), 5.69 (d, 1H, J=2.93 Hz), 3.50 (s, 3H), 3.12 (s, 3H), 2.11 (s, 3H). 13C NMR (DMSO): 159.2, 153.1, 151.9, 151.9, 139.2, 131.5, 129.6, 129.4, 128.8, 126.9, 124.3, 122.8, 120.6, 118.2, 117.6, 111.9, 108.9, 107.1, 105.2, 47.8, 32.3, 28.2, 13.9. HRMS (ES+) (m/z): [M+1]+ calculated for C26H23N4O3, 439.1765. found, 439.1771.

Workup

customA white product was isolated
washwashed
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-fab8ba3fde0b4325b5ef4e0176815815
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609661B2

Reaction notes

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