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

HRID 904547Notes

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]([O:21][CH3:22])=[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]([O:21][CH3:22])=[O:20])[CH:15]=[CH:14][C:13]3=[N:1][C:2]=2[CH:6]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 5 g (0.0292 mol) of 3-amino-5-methyl-2-thiophenecarboxylic acid, methyl ester (German Patent 1055007, April 16, 1959) and 5 g (0.0292 mol) of 6-chloro-3-pyridinecarboxylic acid, methyl ester (Alfred Bader Chemical Company) is heated in an oil bath at 180° C. for thirty minutes. The mixture is cooled, dissolved in hot methanol, cooled and 1.2 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid, methyl ester is collected; mp 215°-216° C. after recrystallization from methanol.

Workup

temperatureThe mixture is cooled
temperaturecooled
custom1.2 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid, methyl ester is collected
custommp 215°-216° C. after recrystallization from methanol

Sources & evidence

ORD record: ord-b2274745c4d2463d90d2bc45610fca97
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230707

Reaction notes

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