Ethanol → 6-Ethoxy-3-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

HRID 373222Notes

Reaction equation

HRID 373222 reaction equation
Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[N:25](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1.[CH2:50]([OH:52])[CH3:51]>[Na]>[CH2:50]([O:52][C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:22][N:23]=[N:24][N:25]=3)=[CH:13][CH:14]=2)[C:6](=[O:45])[N:5]([CH2:46][CH2:47][CH3:48])[C:4](=[O:49])[CH:3]=1)[CH3:51]

Participants

4

Reactant 2

HCID 702EthanolHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1784565426-Ethoxy-3-propyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

6-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.8 g) was dissolved in a solution of sodium metal (69 mg) in ethanol (10 mL) and the mixture was heated under reflux for 14 hours with stirring. The reaction mixture was concentrated to dryness and the resulting residue was dissolved in methylene chloride-water. The solution was acidified with 1N hydrochloric acid (1.5 ml), extracted and the organic layer was separated. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give white amorphous powders (0.36 g, 69%). M.p. 108°-119° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionthe resulting residue was dissolved in methylene chloride-water
  5. extractionextracted
  6. customthe organic layer was separated
  7. washThe organic layer was washed with water
  8. customdried
  9. customevaporated to dryness
  10. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c57a35253f8f4120b2ef895bbd6e110c
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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