6-Chloronicotinic acid → 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid

HRID 904509Notes

Reaction equation

HRID 904509 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=O.Cl[C:19]1[N:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1>>[O:9]=[C:7]1[N:24]2[CH:23]=[C:22]([C:25]([OH:27])=[O:26])[CH:21]=[CH:20][C:19]2=[N:1][C:2]2[S:3][C:4]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:5][C:6]1=2

Participants

3

Reactant 2

HCID 792226-Chloronicotinic acidHCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylate

Product 1

HCID 128623554-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acidYield 6.2%

Procedure

From 5.0 g (0.02 mol) of 2-amino-5-phenyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966) and 3.2 g (0.02 mol) of 6-chloro-3-pyridinecarboxylic acid (Aldrich Chemical Company), following the procedure of Example 3, there is obtained 0.4 g of 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid; mp 387°-392° C. after recrystallization from pyridine.

Sources & evidence

ORD record
ord-bf5a499167ba4259b0888b901b38da3a
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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