Propylamine → HCID 178456798, compound

HRID 373228Notes

Reaction equation

HRID 373228 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(CCC)[C:4](=[O:49])[CH:3]=1.[CH2:50]([NH2:53])[CH2:51][CH3:52]>C(O)C>[CH2:50]([N:53]1[C:4](=[O:49])[CH:3]=[C:2]([NH:7][CH2:2][CH2:3][CH3:4])[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[NH:25][N:24]=[N:23][N:22]=3)=[CH:11][CH:10]=2)[C:6]1=[O:45])[CH2:51][CH3:52]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 178456798HCID 178456798, compoundYield 173.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (1.0 g) and propylamine (0.19 g) in ethanol (20 ml) was heated under reflux for 18 hours with stirring. The reaction mixture was concentrated to dryness and then the residue was extracted with methylene chloride-dilute hydrochloric acid. The organic layer was washed with water, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give pale yellow powders (0.58 g, 83%).

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. extractionthe residue was extracted with methylene chloride-dilute hydrochloric acid
  4. washThe organic layer was washed with water
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7e18f13a93b84f118e9057431abf65d3
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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