Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

HRID 426204Notes

Reaction equation

HRID 426204 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:9][C:10]1[NH:15][C:14](=[O:16])[NH:13][C:12](=[O:17])[C:11]=1[CH:18]([CH3:20])[CH3:19].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>O.CC(C)=O>[CH:18]([C:11]1[C:12](=[O:17])[NH:13][C:14](=[O:16])[NH:15][C:10]=1[O:9][C:8]1[CH:7]=[C:6]([CH:23]=[C:22]([CH3:24])[CH:21]=1)[CH:2]=[O:1])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 591846836-(3-[1,3]Dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione

Product 1

HCID 591848043-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yloxy)-5-methyl-benzaldehydeYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 6-(3-[1,3]dioxolan-2-yl-5-methyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (1.33 g, 4 mmol), PPTS (201 mg, 0.8 mmol), and water (10 drops) in acetone (20 ml) was heated under reflux for 4 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, CHCl3: methanol (95:5)) to afford 1.03 g (89%) of a white solid. m.p. 241-242° C.; 1H NMR (200 MHz, CD3OD/CDCl3) δ 1.03 (6H, d, J=7.2 Hz), 2.34 (3H, s), 2.84 (1H, m), 6.99 (1H, s), 7.17 (1H, s), 7.38 (1H, s), 9.81 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. customthe mixture was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent, CHCl3: methanol (95:5))

Sources & evidence

ORD record
ord-fb20f7d984174e7d97213f1d595a5b06
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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