6-Chloronicotinamide → 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxamide

HRID 904548Notes

Reaction equation

HRID 904548 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]([NH2:21])=[O:20])=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH3:7][C:5]1[S:4][C:3]2[C:8](=[O:10])[N:18]3[CH:17]=[C:16]([C:19]([NH2:21])=[O:20])[CH:15]=[CH:14][C:13]3=[N:1][C:2]=2[CH:6]=1

Participants

4

Reactant 2

HCID 804566-ChloronicotinamideHCID 8189523-Amino-5-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 129530542-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxamideYield 14.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2.7 g (0.0158 mol) of 3-amino-5-methyl-2-thiophenecarboxylic acid, methyl ester (German Patent 1055007, April 16, 1959) and 2.5 g (0.0158 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) is heated in an oil bath at 180°-190° C. for one hour. The mixture is cooled and then suspended in hot chloroform and filtered to give 0.6 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxamide; mp 375°-377° C. after recrystallization from pyridine.

Workup

  1. temperatureis heated in an oil bath at 180°-190° C. for one hour
  2. temperatureThe mixture is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ba9ba352267a441fbb588e49438ae9c8
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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