N-methyl-2-pyrrolidone → HCID 135767476, compound

HRID 1762078Notes

Reaction equation

HRID 1762078 reaction equation
[C:1](=O)([O:3]C(C)(C)C)N.[NH2:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][CH:13]=[CH:12][N:11]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([NH:25][NH2:26])=O.CN1CCCC1=O>O>[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]1[N:17]=[C:16]2[N:26]([C:1](=[O:3])[NH:9][C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:15]=32)[N:25]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 187312-Furancarboxylic acid, hydrazideHCID 77922tert-Butyl carbamateHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 135767476HCID 135767476, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the tert-butyl carbamate of 2-amino-3-cyanopyridine (4.6 g), 2-furoylhydrazine (2.65 g) and 1-methyl-2-pyrrolidone (46 mL) is heated at 160° over 18 hr. It is cooled and diluted with water (369 mL) to afford 2-(2-furyl)pyrido-[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidin-5(6H)one in 53% yield. It is purified by tituration in hot methanol, which removes the soluble impurities, and melts above 360° C.

Workup

  1. temperatureis heated at 160° over 18 hr
  2. temperatureIt is cooled

Sources & evidence

ORD record
ord-b7547a62c5344ea991c13568cfc00036
Source dataset
uspto-grants-1989_05
Patent number
US04831013

Reaction notes

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