Methyl 6-chloropyridine-3-carboxylate → HCID 12953062, compound

HRID 904552Notes

Reaction equation

HRID 904552 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7].Cl[C:14]1[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1>CO>[CH3:8][C:4]1[S:5][C:6]([CH3:7])=[C:2]2[C:3]=1[C:9](=[O:11])[N:19]1[CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=[CH:15][C:14]1=[N:1]2

Participants

4

Reactant 2

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 11019562Methyl 4-amino-2,5-dimethylthiophene-3-carboxylate

Product 1

HCID 12953062HCID 12953062, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2.5 g (0.0113 mol) of 4-amino-2,5-dimethyl-3-thiophenecarboxylic acid, methyl ester and 2.5 g (0.0113 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 0.3 g of 1,3-dimethyl-10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid, methyl ester is collected; mp 209°-210° C. after recrystallization from methanol.

Workup

  1. temperatureThe mixture is cooled
  2. temperaturecooled
  3. custom0.3 g of 1,3-dimethyl-10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid, methyl ester is collected
  4. custommp 209°-210° C. after recrystallization from methanol

Sources & evidence

ORD record
ord-2718f85acbf84a7d8f59c0ec836a2266
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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