Methanol → HCID 13589522, compound

HRID 2073617Notes

Reaction equation

HRID 2073617 reaction equation
CO.O.[CH3:4][C:5]1([C:10]2[CH:11]=[C:12]([CH:16]3[N:21]4[CH:22]=[CH:23][N:24]=[C:20]4[NH:19][C:18]([CH3:25])=[C:17]3[C:26]([O:28][CH3:29])=[O:27])[CH:13]=[CH:14][CH:15]=2)OCC[O:6]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:5]([C:10]1[CH:11]=[C:12]([CH:16]2[N:21]3[CH:22]=[CH:23][N:24]=[C:20]3[NH:19][C:18]([CH3:25])=[C:17]2[C:26]([O:28][CH3:29])=[O:27])[CH:13]=[CH:14][CH:15]=1)(=[O:6])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13589523HCID 13589523, compound

Product 1

HCID 13589522HCID 13589522, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

In a mixture of 50 ml of acetone, 30 ml of methanol and 20 ml of water is dissolved 1.8 g of 5-[3-(2-methyl-1,3-dioxolan-2-yl)phenyl]-6-methoxycarbonyl-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine. The mixture is adjusted to pH 1 with p-toluenesulfonic acid and then heated at 60° C. for 3 hours. The solvent is distilled off and the residue is neutralized with sodium bicarbonate solution. The resulting white precipitations are collected by filtration and recrystallized from a mixture of ethanol and acetone to give 1.1 g of 5-(3-acetylphenyl)-6-methoxycarbonyl-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine, melting at 227°-229° C.

Workup

  1. distillationThe solvent is distilled off
  2. customThe resulting white precipitations
  3. filtrationare collected by filtration
  4. customrecrystallized from a mixture of ethanol and acetone

Sources & evidence

ORD record
ord-52d2e696c0dc46d6b947671adf47baba
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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