Phenyl glycidyl ether → HCID 70454145, compound

HRID 1903790Notes

Reaction equation

HRID 1903790 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1O[CH2:3]1.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH3:27])[C:18](=[O:26])[N:19]([CH3:25])[C:20](=[O:24])[C:21]=1[CH2:22][CH3:23].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(Cl)Cl.C(OCC)(=O)C>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([O:33][CH:2]([CH2:3][NH:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH3:27])[C:18](=[O:26])[N:19]([CH3:25])[C:20](=[O:24])[C:21]=1[CH2:22][CH3:23])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:32]

Participants

6

Reactant 3

HCID 31217Phenyl glycidyl etherHCID 444972Fumaric AcidHCID 20237901HCID 20237901, compound

Product 1

HCID 70454145HCID 70454145, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3.3 g. Phenyl glycidyl ether and 10 g. 4-(2-aminoethylamino)-1,3-dimethyl-5-ethylpyrimidine-2,6(1H,3H)-dione are mixed and left to stand for 24 hours at ambient temperature. The reaction mixture is dissolved in methylene chloride and purified chromatographically with silica gel, using the elution agent methylene chloride-ammonia-saturated methanol (9:1 v/v). By evaporation of the pure fractions, there are obtained 5.5 g. of a yellowish oil. This is dissolved in ethyl acetate, whereafter a solution of 1.7 g. fumaric acid in ethyl acetate is added thereto. After crystallization has taken place, the crystals are filtered off with suction and recrystallized from ethanol. There are obtained 2.8 g. (26% of theory) of the desired product in the form of colorless crystals; m.p. 138°-139° C. (bubble formation).

Workup

  1. waitleft
  2. custompurified chromatographically with silica gel
  3. customBy evaporation of the pure fractions, there
  4. customare obtained 5.5 g
  5. customAfter crystallization
  6. filtrationthe crystals are filtered off with suction
  7. customrecrystallized from ethanol
  8. customThere are obtained 2.8 g

Sources & evidence

ORD record
ord-968ad332130f42089f632dd30f734688
Source dataset
uspto-grants-1984_03
Patent number
US04438128

Reaction notes

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