Acetate → 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide

HRID 904529Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH2:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:13][C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:15][C:16]=1[C:17](OCC)=[O:18].CC([O-])=O>>[O:18]=[C:17]1[N:7]2[CH:6]=[C:5]([C:8]([NH2:10])=[O:9])[CH:4]=[CH:3][C:2]2=[N:11][C:12]2[S:13][C:14]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][C:16]1=2

Participants

Reactant 3

HCID 175Acetate

HCID 804566-Chloronicotinamide

HCID 638860ethyl 2-amino-5-phenylthiophene-3-carboxylate

Product 1

HCID 128623674-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamideYield 4.1%

Procedure

From 4.7 g (0.030 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 7.5 g (0.030 mol) of 2-amino-5-phenyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966), following the procedure of Example 22, there is obtained 0.4 g of 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide, monoacetate; mp 348°-352° C. after recrystallization from glacial acetic acid.

Sources & evidence

ORD record: ord-893ab790e9ed4fa29744aa97721bbdde
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230707

Reaction notes

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