Hydrochloric Acid → 4-(3-bromo-5-fluoro-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 401109Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=O.[C:12]1([C:18](=O)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH2:27][C:28]([NH2:30])=[O:29].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:30][C:28](=[O:29])[NH:27]2)[CH:7]=[C:8]([F:11])[C:9]=1[OH:10]

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of 3-bromo-5-fluoro-4-hydroxybenzaldehyde (Intermediate 77) (600 mg, 2.7 mmol), 1,2-diphenylethanone (538 mg, 2.7 mmol), urea (493 mg, 8.2 mmol) and conc HCl (1 mL) in ethanol (4 mL) was heated at 95° C. for 50 hours. The mixture was evaporated under reduced pressure and was purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1) to give product (400 mg, yield 33%) as yellow solid. 1H NMR (DMSO 300 MHz): δ 10.41 (brs, 1H), 8.66 (s, 1H), 7.45 (s, 1H), 7.24-6.95 (m, 10H), 6.75 (d, J=7.8 Hz, 2H), 5.07 (s, 1H).

Workup

customThe mixture was evaporated under reduced pressure
customwas purified by silica gel column chromatography (petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record: ord-4b4850cf622044d3be1bc15a9bae26ff
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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