Hydrochloric Acid → 4-(3-(isoxazol-4-yl)phenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 401066Notes

Reaction equation

[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:16]1[CH:20]=[C:19]([C:21]2[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=2)[CH:24]=O)[CH:18]=[N:17]1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[O:16]1[CH:20]=[C:19]([C:21]2[CH:22]=[C:23]([CH:24]3[C:8]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[NH:32][C:30](=[O:31])[NH:29]3)[CH:26]=[CH:27][CH:28]=2)[CH:18]=[N:17]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1,2-diphenylethanone (46 mg, 0.233 mmol), 3-(isoxazol-4-yl)benzaldehyde (Intermediate 46) (36 mg, 0.209 mmol) and urea (48 mg, 0.627 mmol) in EtOH (10 mL) was added concentrated HCl (0.4 mL). The mixture was stirred at 85° C. for 14 h. The volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography (PE:EA=1:1) to afford Compound 91 as an off-white power (18 mg, 22.2%). 1H NMR (MeOH-d4 500 MHz): δ 8.99 (s, 1H), 8.74 (s, 1H), 7.50-7.53 (m, 2H), 7.39-7.50 (m, 2H), 7.23-7.25 (m, 5H), 7.00-7.02 (m, 2H), 6.84-6.87 (m, 2H), 5.35 (s, 1H); MS (ESI): m/z 394.1 [M+1]+.

Workup

customThe volatiles were removed under reduced pressure
customthe residue was purified by silica gel column chromatography (PE:EA=1:1)

Sources & evidence

ORD record: ord-37f872480bf443a9a618cd7e2719940a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741915B2

Reaction notes

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