Triethylamine → Ethyl 5-methyl-7-(3-methylbenzo[b]thiophen-2-yl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate

HRID 1020281Notes

Reaction equation

HRID 1020281 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][N:3]=1.C(N(CC)CC)C.[CH3:14][C:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[S:17][C:16]=1[CH:24]=O.[CH2:26]([O:28][C:29](=[O:34])[CH2:30][C:31]([CH3:33])=O)[CH3:27]>C(O)C>[CH3:33][C:31]1[NH:1][C:2]2[N:3]([N:4]=[N:5][N:6]=2)[CH:24]([C:16]2[S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:15]=2[CH3:14])[C:30]=1[C:29]([O:28][CH2:26][CH3:27])=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8868Ethyl AcetoacetateHCID 5199183-Methylbenzo(b)thiophene-2-carboxaldehydeHCID 178509299HCID 178509299, compound

Product 1

HCID 135959879Ethyl 5-methyl-7-(3-methylbenzo[b]thiophen-2-yl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 5-aminotetrazole (850 mg; 10.0 mmole) was dissolved in hot ethanol (25 ml) with triethylamine (1.8 mmole; 0.25 ml). When all solids were dissolved (about ten minutes of heating at 82° C.), 3-methyl-2-benzothiophenecarboxaldehyde (1.76 g; 10.0 mmole) was added followed by ethylacetoacetate (1.28 ml; 10.0 mmole). The clear solution was maintained at reflux for 15 h. At which time a white precipitate had filled the flask and the mixture was cooled to room temperature where it was filtered and the material washed with ethanol then ethyl ether to provide the desired product (1.42 g; 41%) as a white powder. 1H NMR (400 MHz; CDCl3) d 11.2 (bs, 1H); 7.73 (d, 1H, J=7.8 Hz); 7.69 (d, 1H, J=7.8 Hz); 7.39 (ddd, 1H, J=7.0, 7.0, 0.78 Hz); 7.32 (ddd, 1H, J=8.2, 7.0, 1.5 Hz); 4.17-4.05 (m, 2H); 2.71 (s, 3H); 2.69 (s, 3H); 1.14 (at, J=7.0 Hz). LC MS shows MH+ at 356 and 2 MH+ at 711.

Workup

  1. dissolutionWhen all solids were dissolved
  2. additionwas added
  3. temperatureThe clear solution was maintained
  4. temperatureat reflux for 15 h
  5. additionAt which time a white precipitate had filled the flask
  6. filtrationwas filtered
  7. washthe material washed with ethanol

Sources & evidence

ORD record
ord-e4798d2b93e1477d8fdac6777e98c585
Source dataset
uspto-grants-2014_05
Patent number
US08716319B2

Reaction notes

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