Ethyl Acetoacetate → HCID 178429546, compound

HRID 2222577Notes

Reaction equation

HRID 2222577 reaction equation
C(O[C:4](=[O:9])[CH2:5][C:6](=O)[CH3:7])C.[C:10]1([NH:16][C:17]([NH:19][C:20]([NH2:22])=[NH:21])=[NH:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH3:7][C:6]1[N:21]=[C:20]([NH:19][C:17]([NH:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[NH:18])[NH:22][C:4](=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178513035HCID 178513035, compound

Product 1

HCID 178429546HCID 178429546, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 milliliter round-bottom flask, 3-oxobutyric acid ethyl ester (2.6 grams, 0.020 mol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) was added at room temperature to a solution of 1-phenylbiguanide (3.5 grams, 0.020 mol, prepared as described in Part D of Example I) in anhydrous ethanol (15 milliliters). The mixture was heated at reflux and stirred for 4 hours. After a few minutes, all the components dissolved. Cooling the resulting yellow solution mixture to room temperature gave a colorless precipitate. The precipitate was isolated by filtration and thoroughly washed with water, then with cold ethanol (0° C.), and finally with hexanes. The solid was then recrystallized from anhydrous ethanol, recovered by filtration, and dried under reduced pressure to give the targeted N-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)-N′-phenylguanidine as a colorless solid (3.60 grams, 74 percent yield): mp=265° C.; 1H NMR (DMSO-d6, 303 K) δ: 11.19 (s, 1H), 9.05 (s, 1H), 9.5-6.5 (br, 2H), 7.65 (d, 2H, 3J=7.7 Hz), 7.26 (m, 2H), 7.00 (t, 1H, 3J=7.3 Hz), 5.60 (s, 1H), 2.09 (s, 3H); 13C NMR (DMSO-d6, 303 K) δ: 164.0, 163.2, 158.3, 156.2, 138.9, 128.8, 122.7, 120.7, 103.7, 23.6. Exact mass calculated for C12H13N5O=243.1120. Measured High Resolution Mass Spectrum (MAB/HR/N2)=243.1120. Anal. Calcd for C12H13N5O: C, 59.25; H, 5.39; N, 28.79. Found: C, 59.17; H, 5.39; N, 29.04.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. waitAfter a few minutes
  4. dissolutionall the components dissolved
  5. customgave a colorless precipitate
  6. customThe precipitate was isolated by filtration
  7. washthoroughly washed with water
  8. customwith cold ethanol (0° C.)
  9. customThe solid was then recrystallized from anhydrous ethanol
  10. filtrationrecovered by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-a4b6dce1c428438b8d2e22afae7b3392
Source dataset
uspto-grants-2008_05
Patent number
US07371858B2

Reaction notes

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