o-Vanillin → HCID 136400708, compound

HRID 1367639Notes

Reaction equation

HRID 1367639 reaction equation
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[C:5]([CH3:15])=[C:4]([CH3:16])[N:3]=1.O=[CH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:22]([O:23][CH3:24])[C:20]=1[OH:21]>CC(O)=O>[OH:21][C:20]1[C:22]([O:23][CH3:24])=[CH:25][CH:26]=[CH:27][C:19]=1[CH:18]=[CH:1][C:2]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6](=[O:14])[C:5]([CH3:15])=[C:4]([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 8991o-VanillinHCID 58306049HCID 58306049, compound

Product 1

HCID 136400708HCID 136400708, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,5,6-trimethyl-3-phenylpyrimidin-4(3H)-one (4) (403 mg, 1.88 mmol) and O-vanillin (286 mg, 1.88 mmol) in AcOH (4 mL) was heated at 150° C. for 2 h in a microwave oven. Acetic acid was evaporated under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 1:1) to afford 5 as a yellow solid (380 mg, 58%); MS m/z: 349 [M+H]+.

Workup

  1. customAcetic acid was evaporated under reduced pressure
  2. customthe product was purified by column chromatography (EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-1808682c74764a7d937ec7c7bda00b79
Source dataset
uspto-grants-2011_02
Patent number
US07893260B2

Reaction notes

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