Hydrochloric Acid → 6-(3-Chloro-5-methyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione

HRID 426126Notes

Reaction equation

HRID 426126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([O:20]C)[N:14]=[C:13]([O:22]C)[N:12]=2)=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[C:9]([C:11]1[NH:12][C:13](=[O:22])[NH:14][C:15](=[O:20])[C:16]=1[CH:17]([CH3:18])[CH3:19])=[O:10]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59184800(3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

Product 1

HCID 213032376-(3-Chloro-5-methyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dioneYield 97.8%

Procedure

(3-Chloro-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone (49) (3.4 g, 10 mmol) was refluxed with concentrated HCl (35 ml) for 4 hr. After cooling to room temperature, the white precipitate was collected by filtration, washed with cold water and hexane, and dried in high vacuo to afford 3 g (97%) of a white solid. m.p. 254-255° C.; 1H NMR (200 MHz, CDCl3/CD3OD) δ: 1.17 (6H, d, J=6.9 Hz), 2.25-2.45 (4H, m), 7.50-7.71 (3H, m); HRMS (EI): Calc. 306.077120, Found 306.076851.

Workup

  1. filtrationthe white precipitate was collected by filtration
  2. washwashed with cold water and hexane
  3. customdried in high vacuo

Sources & evidence

ORD record
ord-43e78151cfa54649b882dfbaa1812ab5
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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