Pyridine → 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carbonitrile

HRID 1155897Notes

Reaction equation

HRID 1155897 reaction equation
[CH3:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]3[CH:12]=[C:13]([C:16]([NH2:18])=O)[CH:14]=[CH:15][C:6]3=[N:5][C:4]=2[CH:3]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]3[CH:12]=[C:13]([C:16]#[N:18])[CH:14]=[CH:15][C:6]3=[N:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 129530542-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxamide

Product 1

HCID 129530552-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxamide (Example 44), 0.6 g (0.0023 mol), in 10 of pyridine, 25 ml of phosphorous oxychloride and 25 ml of chloroform is refluxed on a steam bath for three hours. The solvents are evaporated in vacuo and the residue is treated with 100 ml of ice water. The resulting precipitate is filtered to give 0.5 g of 2-methyl-10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carbonitrile; mp 258°-259° C. after recrystallization from methanol.

Workup

  1. customThe solvents are evaporated in vacuo
  2. additionthe residue is treated with 100 ml of ice water
  3. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-9d869a94cbc04e69993ce8a74ac79d11
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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