Ethyl orthoformate → 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

HRID 1415137Notes

Reaction equation

HRID 1415137 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:16])=[N:8][C:9]([NH:14][CH3:15])=[C:10]([NH2:13])[C:11]=1[Cl:12])=[O:5])[CH3:2].[CH2:17](OC(OCC)OCC)C>>[CH2:1]([O:3][C:4]([C:6]1[C:11]([Cl:12])=[C:10]2[N:13]=[CH:15][N:14]([CH3:17])[C:9]2=[N:8][C:7]=1[CH3:16])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 123876175-Amino-6-methylamino-4-chloro-2-methylpyridine-3-carboxylic acid ethyl ester

Product 1

HCID 123876407-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester

Procedure

2.4 g. of 5-Amino-6-methylamino-4-chloro-2-methylpyridine-3-carboxylic acid ethyl ester (0.01 mol.) and 10 ml. of orthoformic acid triethyl ester are refluxed for 12 hours. After the excess ortho ester has been removed, the residue is recrystallized from ethyl acetate to obtain 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester, m.p. 56°-58° . Yield 2.2 g. (88%).

Workup

  1. customAfter the excess ortho ester has been removed
  2. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5213ed78a62442e58e96ba9fed0284ea
Source dataset
uspto-grants-1977_01
Patent number
US04003908

Reaction notes

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