N-Methylbutylamine → HCID 178448980, compound

HRID 373229Notes

Reaction equation

HRID 373229 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.[CH3:50][NH:51][CH2:52][CH2:53][CH2:54][CH3:55]>C(O)C>[CH3:50][N:51]([CH2:52][CH2:53][CH2:54][CH3:55])[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[NH:22][N:23]=[N:24][N:25]=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

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 198115276-Chloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)-biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 178448980HCID 178448980, compoundYield 73%

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 (0.5 g) and N-methylbutylamine (0.2 g) in ethanol (10 ml) was heated under reflux for 8 hours. 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 amorphous powders (0.26 g, 73%).

Workup

  1. temperatureunder reflux for 8 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-474f768596be497bb1eb6958a32f1197
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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