Hydrochloric Acid → 4-(8-nitro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 2177945Notes

Reaction equation

[N+:1]([C:4]1[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=[C:6]([CH:14]=O)[CH:5]=1)([O-:3])=[O:2].[C:16]1([C:22](=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:31][C:32]([NH2:34])=[O:33].Cl>C(O)C>[N+:1]([C:4]1[C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=[C:6]([CH:14]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:34][C:32](=[O:33])[NH:31]2)[CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 77 °C

Procedure

A mixture of 8-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde (Intermediate 45) (110 mg, 0.529 mmol), 1,2-diphenylethanone (103.8 mg, 0.529 mmol), urea (95.2 mg, 1.587 mmol), and concentrated hydrochloric acid (0.1 mL) in ethanol (10 mL) was refluxed at 77° C. for 63 h. Volatiles were removed, and purified by preparative HPLC to give Compound 89 (12.1 mg, yield 5.5%). 1H NMR (CD3OD 400 MHZ): δ 7.32 (s, 1H), 7.14 (s, 5H), 7.06 (s, 1H), 6.95-6.94 (m, 3H), 6.78-6.76 (m, 2H), 5.20 (s, 1H), 4.26-4.24 (m, 4H); MS (ESI): m/z 430.0 [M+H]+.

Workup

customVolatiles were removed
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-9fd25736e6524163b53fd6683e50a678
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067893B2

Reaction notes

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