4-Aminopyridine → Ethyl 4-(propylamino)-2-(3-(pyridin-4-yl)ureido)pyrimidine-5-carboxylate

HRID 2284698Notes

Reaction equation

O([C:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][N:12]=1)=[O:9])C1C=CC=CC=1.[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.CN(C)C=O>O>[CH2:18]([NH:17][C:15]1[C:14]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][N:12]=[C:11]([NH:10][C:8]([NH:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[O:9])[N:16]=1)[CH2:19][CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

To ethyl 2-((phenoxycarbonyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (E7, 2.89 g) and 4-aminopyridine (3.16 g), N,N-dimethylformamide (30 mL) was added at room temperature, and the mixture was stirred at 70° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then the reaction mixture was poured into water (300 mL). The solid matter was taken by filtration, and purified by silica gel column chromatography (eluent, ethyl acetate) to obtain ethyl 4-(propylamino)-2-(3-(pyridin-4-yl)ureido)pyrimidine-5-carboxylate (E8, 830 mg) as white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid matter was taken by filtration
custompurified by silica gel column chromatography (eluent, ethyl acetate)

Sources & evidence

ORD record: ord-81994395a7104e35a615ea6d15c1e6d5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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