Ethyl 2-amino-5-ethyl-3-thenoate → HCID 12862358, compound

HRID 1155863Notes

Reaction equation

HRID 1155863 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:12][CH3:13])=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl[C:15]1[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1>>[CH2:12]([C:4]1[S:3][C:2]2[N:1]=[C:15]3[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]3[C:7](=[O:9])[C:6]=2[CH:5]=1)[CH3:13]

Participants

3

Reactant 2

HCID 78263Ethyl 2-amino-5-ethyl-3-thenoateHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 12862358HCID 12862358, compound

Procedure

A mixture of 10 g (0.05 mol) of 2-amino-5-ethyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966) and 8.61 g (0.05 mol) of 6-chloro-3-pyridinecarboxylic acid, methyl ester (Alfred Bader Chemical Company) is heated in a wax bath at 178°-188° C. for three hours under nitrogen. The distillate is collected in a Dean-Stark trap attached to the reaction flask. The mixture is cooled, dissolved in hot methanol, cooled and 5.5 g of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid, methyl ester is collected; mp 151°-152° C. after recrystallization from methanol.

Workup

  1. temperatureis heated in a wax bath at 178°-188° C. for three hours under nitrogen
  2. distillationThe distillate is collected in a Dean-Stark trap
  3. temperatureThe mixture is cooled
  4. dissolutiondissolved in hot methanol
  5. temperaturecooled
  6. custom5.5 g of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid, methyl ester is collected
  7. custommp 151°-152° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-64540903ad4f4bbcbf26a82e55c54978
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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