Hydrochloric Acid → 4-(3-methyl-4-nitrophenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one

HRID 422046Notes

Reaction equation

[NH:1]=[C:2]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH3:25])[CH:17]=1)/[CH:3]=[C:4](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH3:15])\[NH2:5].N[C:27](N)=[O:28].Cl>C(O)C.O1CCOCC1>[CH3:25][C:18]1[CH:17]=[C:16]([C:2]2[CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[O:12][CH2:13][CH2:14][CH3:15])[NH:5][C:27](=[O:28])[N:1]=2)[CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of (1Z)-3-imino-3-(3-methyl-4-nitrophenyl)-1-[2-(propyloxy)phenyl]prop-1-en-1-amine (2.20 g, 6.45 mmol) in ethanol (100 mL) was added urea (6.0 g, 100 mmol) and hydrochloric acid in dioxane 4.0 N (25 mL) at room temperature. The reaction mixture was heated to 75° C. for 16 h, at which time it was concentrated in vacuo, diluted with water (200 mL) and adjusted to pH 10 with sodium hydroxide 2.0 N. The product was extracted with chloroform (200 mL) then diluted with hexanes (50 mL) to precipitate the product. The solid was filtered and washed with chloroform/hexanes (1:4) to give 4-(3-methyl-4-nitrophenyl)-6-[2-(propyloxy)phenyl]pyrimidin-2(1H)-one (1.80 g, 81%). MS (EI) for C20H19N4O3: 363 (MH+).

Workup

concentrationwas concentrated in vacuo
additiondiluted with water (200 mL)
extractionThe product was extracted with chloroform (200 mL)
additionthen diluted with hexanes (50 mL)
customto precipitate the product
filtrationThe solid was filtered
washwashed with chloroform/hexanes (1:4)

Sources & evidence

ORD record: ord-a63ac55ff73c4f5696ae17ada3fb06a1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101625B2

Reaction notes

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