Water → (e)-3-(4-Chlorophenyl)-n-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide

HRID 1425647Notes

Reaction equation

[CH:1]1[C:6](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)=[CH:5][CH:4]=[C:3]([Cl:12])[CH:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][N:17]([CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24])[C:16](=[O:28])[N:15]=1.Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C=O>[Cl:12][C:3]1[CH:2]=[CH:1][C:6](/[CH:7]=[CH:8]/[C:9]([NH:13][C:14]2[CH:19]=[CH:18][N:17]([CH2:20][CH:21]([O:22][CH2:23][CH3:24])[O:25][CH2:26][CH3:27])[C:16](=[O:28])[N:15]=2)=[O:11])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

P-chloro cinnamic acid (1.84 g, 10 mM), 4-amino-1-(2,2-diethoxyethyl)-1H-pyrimidin-2-one (b, 3.00 g, 15 mM), 1-hydroxybenztriazolemonohydrate (2.30 g, 15 mM) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.90 g, 15 mM) were suspended in N,N-dimethylformamide (20 mL) and stirred at 70° C. for 5 hours. After the reaction mixture was cooled to room temperature, water (20 mL) was added and stirred at room temperature. The crystal precipitated from the reaction mixture was filtered to afford 2.48 g of the desired compound (E)-3-(4-chlorophenyl)-N-[1-(2,2-diethoxyethyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-acrylamide (c) (yield 68%, colorless crystal).

Workup

temperatureAfter the reaction mixture was cooled to room temperature
stirringstirred at room temperature
customThe crystal precipitated from the reaction mixture
filtrationwas filtered

Sources & evidence

ORD record: ord-6d667ba75eab499d8601ca4de029d744
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933012B2

Reaction notes

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