(3-Bromo-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone → 6-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione

HRID 426109Notes

Reaction equation

HRID 426109 reaction equation
[Br: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>[Br: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 1

HCID 59686860(3-Bromo-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

Product 1

HCID 577518946-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound (27) (34.6 g, 91 mmol) was refluxed with conc. HCl (200 ml) for 3 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 30 g (94%) of a white solid; m.p. 266-267° C.; 1H NMR (200 MHz, DMSO-d6) δ 1.05 (6H, d, J=6.8 Hz), 2.26 (1H, m), 2.40 (3H, s), 7.82 (2H, s), 7.93 (1H, s), 11.02 (1H, s), 11.17 (1H, s).

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-aff84064be8f4e018685395eb3ad1961
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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