Ethanol → 3-cyclopropyl-6-methylamino-1-(3-nitrophenyl)-1H-pyrimidine-2,4-dione

HRID 75629Notes

Reaction equation

Cl[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)[C:6](=[O:17])[N:5]([CH:18]2[CH2:20][CH2:19]2)[C:4](=[O:21])[CH:3]=1.C(O)C.[CH3:25][NH2:26]>CO>[CH:18]1([N:5]2[C:4](=[O:21])[CH:3]=[C:2]([NH:26][CH3:25])[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=3)[C:6]2=[O:17])[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

To the mixture (30 g) of 6-chloro-3-cyclopropyl-1-(3-nitrophenyl)-1H-pyrimidine-2,4-dione 6 and 4-chloro-3-cyclopropyl-1-(3-nitrophenyl)-1H-pyrimidine-2,6-dione 7 obtained in Step 3 were added ethanol (300 ml) and a 40% solution (150 ml) of methylamine in methanol, and the mixture was stirred with heating at 80° C. for 4.5 hrs, ice-cooled and the precipitated solid was filtered by suction. The residue was washed with water (1 liter) and dried to give 3-cyclopropyl-6-methylamino-1-(3-nitrophenyl)-1H-pyrimidine-2,4-dione 8 (16 g, 55%) as a white solid.

Workup

temperatureice-cooled
filtrationthe precipitated solid was filtered by suction
washThe residue was washed with water (1 liter)
customdried

Sources & evidence

ORD record: ord-7a3b9ca16f234b87a409f129181a733a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Reaction notes

Loading…