1-Propanol → HCID 178458743, compound

HRID 373232Notes

Reaction equation

HRID 373232 reaction equation
[Na].ClC1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7](=[O:46])[N:6]([CH2:47][CH2:48][CH3:49])C(=O)C=1.[CH2:51]([OH:54])[CH2:52][CH3:53]>>[CH2:47]([N:6]1[C:51](=[O:54])[CH:52]=[C:53]([O:54][CH2:51][CH2:52][CH3:53])[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]1=[O:46])[CH2:48][CH3:49]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 5360545SodiumHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 178458743HCID 178458743, compoundYield 69%

Procedure

To a solution of sodium (0.09 g) in propanol was added 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.8 g) was added and the mixture was heated under reflux for 14 hours. The reaction mixture was concentrated to dryness. The resulting residue was dissolved in methylene chloride-water. The aqueous layer was acidified with 1N hydrochloric acid and extracted with methylene chloride. 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 colorless amorphous powders (0.38 g, 69%).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 14 hours
  4. concentrationThe reaction mixture was concentrated to dryness
  5. dissolutionThe resulting residue was dissolved in methylene chloride-water
  6. extractionextracted with methylene chloride
  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-5b6b418e743c4177b54a286d8aff045f
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

Loading…