Dimethylbarbituric acid → HCID 68014880, compound

HRID 1747809Notes

Reaction equation

HRID 1747809 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]4[CH2:20][CH2:21][N:22](CC=C)[CH2:23][CH:24]=4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1C(=O)CC(=O)N(C)C1=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[C:1]1([N:7]2[C:11]([C:12]3[C:17](=[O:18])[CH:16]=[CH:15][N:14]([C:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=4)[N:13]=3)=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 68014908HCID 68014908, compound

Product 1

HCID 68014880HCID 68014880, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-(1-phenyl-1H-pyrazol-5-yl)-1-(1-prop-2-en-1-yl-1,2,3,6-tetrahydropyridin-4-yl)pyridazin-4(1H)-one (0.10 g), tetrakis(triphenylphosphine)palladium(0) (50 mg), 1,3-dimethylbarbituric acid (0.13 g) and dichloromethane (5 mL) was heated under reflux for 2 hr under a nitrogen atmosphere, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and recrystallized from 2-propanol/ethyl acetate to give the title compound (32 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr under a nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  5. customrecrystallized from 2-propanol/ethyl acetate

Sources & evidence

ORD record
ord-e27f56a7aac74d62ad45df94237ce31b
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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