Acetic Acid → Ethyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

HRID 1399723Notes

Reaction equation

HRID 1399723 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].[C:5]1([CH3:13])[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.C(O)(=O)C.B(F)(F)F.CCOCC>O1CCCC1.[Cu]Cl>[CH3:18][C:16]1[NH:4][C:2](=[O:3])[NH:1][CH:11]([C:8]2[CH:9]=[CH:10][C:5]([CH3:13])=[CH:6][CH:7]=2)[C:15]=1[C:14]([O:20][CH2:21][CH3:22])=[O:19]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 1176UreaHCID 77254-MethylbenzaldehydeHCID 8000Boron trifluoride etherateHCID 8868Ethyl Acetoacetate

Product 1

HCID 296187Ethyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of urea (2,70 g; 45 mmol), copper (I) chloride (0,297 g; 3 mmol), p-tolualdehyde (3,53 ml; 30 mmol), ethyl acetoacetate (3,81 ml; 30 mmol), acetic acid (0,172 ml; 3 mmol) and boron trifluoride etherate (4,90 ml; 39 mmol) in dry tetrahydrofuran (60 mL) was heated to reflux for 21 h. After cooling to room temperature, the reaction mixture was quenched by adding a saturated solution of sodium hydrogen carbonate and the aqueous solution was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, the residue was suspended in toluene and left standing at room temperature for 24 h. The formed solid was filtered, washed with toluene and dried under reduced pressure to afford 7,45 g (91%) of the title compound as a green solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 21 h
  3. customthe reaction mixture was quenched
  4. additionby adding a saturated solution of sodium hydrogen carbonate
  5. extractionthe aqueous solution was extracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. waitleft
  8. filtrationThe formed solid was filtered
  9. washwashed with toluene
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-6d122363a69243489ed5118bcf6dedbc
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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