Phenyl glycidyl ether → 1-Phenoxy-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol

HRID 365175Notes

Reaction equation

HRID 365175 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[NH2:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH3:26])[C:18](=[O:25])[N:19]([CH3:24])[C:20](=[O:23])[C:21]=1[CH3:22]>CO>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][NH:12][CH2:13][CH2:14][NH:15][C:16]1[N:17]([CH3:26])[C:18](=[O:25])[N:19]([CH3:24])[C:20](=[O:23])[C:21]=1[CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 128188664-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dione

Product 1

HCID 128188591-Phenoxy-3-[2-(1,3,5-trimethylpyrimidine-2,4-dion-6-ylamino)-ethylamino]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.4 g. Phenyl glycidyl ether and 9.6 g. 4-(2-aminoethylamino)-1,3,5-trimethylpyrimidine-2,6(1H,3H)-dione are stirred for about 24 hours at 70° C. The reaction mixture is dissolved in methanol and then separated by column chromatography, using a weakly acidic cation exchanger ("Amberlite" CG 50 II pract. (Serva)). The column is pre-treated with about 1.5 liters 0.1M methanolic triethylammonium acetate solution. The elution agent used is 0.1M methanolic triethylammonium acetate solution. The fractions containing the pure substance are evaporated, then rendered alkaline with 2N aqueous sodium hydroxide solution, extracted with methylene chloride and the extracts dried and evaporated. The light colored oil obtained becomes crystalline upon triturating with diethyl ether. After recrystallized from ethyl acetate, there are obtained 3.6 g. (44% of theory) of the desired product in the form of colorless crystals; m.p. 104°-106° C.

Workup

  1. customseparated by column chromatography
  2. additionThe column is pre-treated with about 1.5 liters 0.1M methanolic triethylammonium acetate solution
  3. additionThe fractions containing the pure substance
  4. customare evaporated
  5. extractionextracted with methylene chloride
  6. customthe extracts dried
  7. customevaporated
  8. customThe light colored oil obtained
  9. customupon triturating with diethyl ether
  10. customAfter recrystallized from ethyl acetate, there
  11. customare obtained 3.6 g

Sources & evidence

ORD record
ord-e4e1197078844e64863b0de58b049910
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

Loading…