Diphenyl Ether → 3-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

HRID 75630Notes

Reaction equation

[CH:1]1([N:4]2[C:9](=[O:10])[CH:8]=[C:7]([NH:11][CH3:12])[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[C:5]2=[O:22])[CH2:3][CH2:2]1.C1(OC2C=CC=CC=2)C=CC=CC=1.[C:36]([O:44]CC)(=O)[CH2:37][C:38]([O:40]CC)=O>>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:38]([OH:40])=[CH:37][C:36](=[O:44])[N:11]([CH3:12])[C:7]=3[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[C:5]2=[O:22])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 7583Diphenyl Ether

HCID 7761Diethyl Malonate

HCID 597172713-cyclopropyl-6-methylamino-1-(3-nitrophenyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 597172003-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trioneYield 51%

Conditions

Temperature: 230 °C

Procedure

To 3-cyclopropyl-6-methylamino-1-(3-nitrophenyl)-1H-pyrimidine-2,4-dione 8 (16 g) obtained in Step 4 were added diphenyl ether (160 ml) and diethyl malonate 9 (40 ml), and the mixture was stirred under heating at 230° C. for 11 hrs while evaporating the resulting ethanol. The reaction mixture was purified by column chromatography (chloroform→chloroform:acetone=9:1) to give 3-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 10 (10 g, 51%) as a brown foamy oil.

Workup

customwhile evaporating the resulting ethanol
customThe reaction mixture was purified by column chromatography (chloroform→chloroform:acetone=9:1)

Sources & evidence

ORD record: ord-5f0abc33679e4b84b4d49b19925fca47
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Reaction notes

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