2-Aminopyridine → HCID 178515422, compound

HRID 1632285Notes

Reaction equation

HRID 1632285 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:8]1[C:12]([CH2:13][C:14]([O:16]CC)=O)=[N:11][N:10]=[N:9]1.[CH:19](OCC)(OCC)OCC.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C(Cl)Cl.C(OCC)C.CO.O>[NH:11]1[C:12]([C:13]2[C:14](=[O:16])[N:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]3=[N:1][CH:19]=2)=[N:8][N:9]=[N:10]1

Participants

8

Reactant 4

HCID 104392-AminopyridineHCID 31214Ethyl orthoformateHCID 6451240Aluminum(III) ChlorideHCID 178470801HCID 178470801, compound

Product 1

HCID 178515422HCID 178515422, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 65911,1,2,2-TetrachloroethaneSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.94 g (10.0 mmole) of 2-aminopyridine, 1.56 g (10.0 mmole) of ethyl tetrazol-5-ylacetate, 1.65 g (11.1 mmole) of triethyl orthoformate and 0.3 g (2.2 mmole) of aluminum chloride in 50 ml of 1,1,2,2-tetrachloroethane was heated at 120° C. under a nitrogen atmosphere for 3 days. The mixture was cooled, diluted to 200 ml with diethyl ether and filtered. The solid obtained was suspended in 100 ml of 1:1 methanol-water. The solid was then separated by filtration and washed with methanol to provide 1.39 g (65%) of off-white-colored solid 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidine-4-one. The infrared spectrum of the product confirmed the structural assignment.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customThe solid obtained
  4. customThe solid was then separated by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-0491038981c847dc8fc4c1c8fb6421ff
Source dataset
uspto-grants-1984_10
Patent number
US04474953

Reaction notes

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