2-Methoxyethanol → 1-(4-aminophenyl)-3-ethyl-2,4(1H,3H)-pyrimidinedione

HRID 2106765Notes

Reaction equation

HRID 2106765 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[CH:7]=[CH:6][N:5]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[C:4]1=[O:19])[CH3:2].S1C=CC=C1.COCCO.[H][H]>CO.[Pt]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([N:5]2[CH:6]=[CH:7][C:8](=[O:9])[N:3]([CH2:1][CH3:2])[C:4]2=[O:19])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 8030ThiopheneHCID 151254793-ethyl-1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 151254801-(4-aminophenyl)-3-ethyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 28.4 parts of 3-ethyl-1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedione, 5 parts of a solution of thiophene in methanol 4% and 500 parts of 2-methoxyethanol was hydrogenated at normal pressure and at 50° C. with 3 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was concentrated to a volume of about 150 parts. After cooling, the product was filtered off (the filtrate was set aside) and dried in vacuo at 60° C., yielding a first fraction of 16.5 parts of 1-(4-aminophenyl)-3-ethyl-2,4(1H,3H)-pyrimidinedione (int. 25). The filtrate, which was set aside (see above), was evaporated. The residue was stirred in methanol. The product was filtered off and dried in vacuo at 60° C., yielding a second fraction of 5.7 parts of int. 20. Total yield: 22.2 parts (88.3%) of int. 25; mp. 190.8° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationthe filtrate was concentrated to a volume of about 150 parts
  3. temperatureAfter cooling
  4. filtrationthe product was filtered off (the filtrate
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-0055a2464ee64178bad4f93361ae832b
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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