Triethylamine → 1-(3-n-butoxy-2-hydroxypropyl)-5,5-dipropyl-(1H,3H,5H)pyrimidine-2,4,6-trione

HRID 257407

Reaction equation

HRID 257407 reaction equation
[CH2:1]([C:4]1([CH2:13][CH2:14][CH3:15])[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]1=[O:12])[CH2:2][CH3:3].C(N(CC)CC)C.[CH2:23]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:24]1[O:26][CH2:25]1>CN(C)C=O.O>[CH2:28]([O:27][CH2:23][CH:24]([OH:26])[CH2:25][N:8]1[C:9](=[O:10])[C:4]([CH2:1][CH2:2][CH3:3])([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[NH:6][C:7]1=[O:11])[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 17049Butyl glycidyl etherHCID 75192Propylbarbital

Product 1

HCID 197831291-(3-n-butoxy-2-hydroxypropyl)-5,5-dipropyl-(1H,3H,5H)pyrimidine-2,4,6-trioneYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5,5 dipropyl-(1H,3H,5H)-pyrimidine-2,4,6-trione (30.8 g, 0.15 mole) in dimethylformamide (30 ml) containing triethylamine (2.02 g, 0.2 mole) was mixed with butyl glycidyl ether (13 g, 0.1 mole). The mixture was heated at 60° C. for 6 hours. The solution was then diluted with water (150 ml) and extracted with toluene (2×50 ml). The organic layer was separated, washed with water (2×100 ml) dried and extracted with 5% aqueous sodium carbonate (6×100 ml). The toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml), the aqueous layers separated, washed with toluene (100 ml) and the pH was adjusted to 3 with sulphuric acid. The precipitated oily product was extracted with toluene (100 ml), and the organic layer was separated, washed with water, dried and evaporated to yield the title compound (16.3 g; 51.6%); purity by HPLC 96.5%.

Workup

  1. extractionextracted with toluene (2×50 ml)
  2. customThe organic layer was separated
  3. washwashed with water (2×100 ml)
  4. customdried
  5. extractionextracted with 5% aqueous sodium carbonate (6×100 ml)
  6. extractionThe toluene phase was then extracted with 1M aqueous sodium hydroxide (2×100 ml)
  7. customthe aqueous layers separated
  8. washwashed with toluene (100 ml)
  9. extractionThe precipitated oily product was extracted with toluene (100 ml)
  10. customthe organic layer was separated
  11. washwashed with water
  12. customdried
  13. customevaporated

Sources & evidence

ORD record
ord-1bb05ed9d92a4f0dad6b0a004d77fbae
Source dataset
uspto-grants-1993_11
Patent number
US05262402

Linked notes

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