2,6-Diaminopyridine → 5,7-Dimethyl-1,8-naphthyridin-2-ylamine

HRID 1395273Notes

Reaction equation

HRID 1395273 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[CH3:9][C:10](=O)[CH2:11][C:12](=O)[CH3:13]>>[NH2:8][C:4]1[N:3]=[C:2]2[C:7]([C:10]([CH3:9])=[CH:11][C:12]([CH3:13])=[N:1]2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 88612,6-DiaminopyridineHCID 31261Acetylacetone

Product 1

HCID 973655,7-Dimethyl-1,8-naphthyridin-2-ylamine

Procedure

Preparation of the compounds having the formula: ##STR3## wherein R' is CH3, OH or CF3 is carried out by (a) condensing 2,6-diaminopyridine with 2,4-pentanedione to yield 7-amino-2,4-dimethyl-1,8-naphthyridine, (b) acetylating the naphthyridine to form the corresponding 7-acetamido naphthyridine, (c) methylating the 7-acetamido compound of step (b) to form a 1,2,4-trimethyl product, (d) hydrogenating the step (c) product to yield 7-acetamido-1,2,4-trimethyl-1,2,3,4-tetrahydro-1,8-naphthyridine, (e) hydrolyzing the product of step (d) under basic conditions and (f) condensing the product of step (e) with a β-diketone of the formula R'COCH2CO2H5 wherein R' is CH3, CH3 or OC2H5.

Workup

  1. customPreparation of the compounds

Sources & evidence

ORD record
ord-800209f2f1bb4515ac091cd67c39caf4
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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