6-Chloronicotinic acid → 2-Methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid

HRID 1155895Notes

Reaction equation

HRID 1155895 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[S:4][C:3]=1[C:8]([O:10]C)=O.Cl[C:13]1[N:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1>CO>[CH3:7][C:5]1[S:4][C:3]2[C:8](=[O:10])[N:18]3[CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=[CH:14][C:13]3=[N:1][C:2]=2[CH:6]=1

Participants

4

Reactant 2

HCID 792226-Chloronicotinic acidHCID 8189523-Amino-5-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 129530522-Methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.7 g (0.01 mol) of 3-amino-5-methyl-2-thiophenecarboxylic acid, methyl ester (German Pat. No. 1055007, Apr. 16, 1959) and 1.6 g (0.01 mol) of 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company) is heated in an oil bath at 180° C. for two hours. The mixture is cooled, dissolved in hot methanol, cooled and 0.23 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid is collected; mp 338°-340° C. after recrystallization from methanol.

Workup

  1. temperatureThe mixture is cooled
  2. temperaturecooled
  3. custom0.23 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid is collected
  4. custommp 338°-340° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-921a81eb7df8469a89c9ca1341005d7b
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

Loading…