Ethylene Glycol → HCID 20183305, compound

HRID 255714Notes

Reaction equation

HRID 255714 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(O)C[OH:30].O.C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([O:25][CH2:26][CH2:27][OH:30])=[O:24]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 8857Ethyl AcetateHCID 15147485HCID 15147485, compound

Product 1

HCID 20183305HCID 20183305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (2 g) and ethyleneglycol (8 ml) was stirred for 50 hours at 90°. The reaction mixture was poured into a mixture of water (50 ml), ethyl acetate (50 ml) and tetrahydrofuran (50 ml). The solvent was distilled off. The residue was chromatographed on silica gel, eluting with a mixture of n-hexane and ethyl acetate (10:1). The fractions containing the object compound were combined and concentrated in vacuo. The crystalline residue was recrystallized from diethyl ether to afford 2-hydroxyethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate.

Workup

  1. distillationThe solvent was distilled off
  2. customThe residue was chromatographed on silica gel
  3. washeluting with a mixture of n-hexane and ethyl acetate (10:1)
  4. additionThe fractions containing the object compound
  5. concentrationconcentrated in vacuo
  6. customThe crystalline residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-402dd33a96514b61969dac4bbacc2b6c
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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