Hydrochloric Acid → HCID 178422236, compound

HRID 904537Notes

Reaction equation

HRID 904537 reaction equation
[CH3:1][C:2]1[S:17][C:5]2[N:6]=[C:7]3[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[CH3:1][C:2]1[S:17][C:5]2[N:6]=[C:7]3[CH:14]=[CH:13][C:12]([C:15]4[NH:20][N:19]=[N:18][N:16]=4)=[CH:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 128623692-Methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carbonitrile

Product 1

HCID 178422236HCID 178422236, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (0.0062 mol) of 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carbonitrile (Example 27), 1.36 g (0.021 mol) of sodium azide and 1.24 g (0.023 mol) of ammonium chloride in 280 ml of dimethylformamide is heated at 110°-120° C. for twelve hours. The reaction mixture is cooled, poured into 1 l of ice water and acidified with concentrated hydrochloric acid. The resulting precipitate is filtered and dissolved in hot glacial acetic acid, activated charcoal (Darco-G60, Matheson, Coleman and Bell) is added and the hot suspension is filtered through Supercell Hyflo® (Johns-Manville). The filtrate is cooled to give 0.1 g of 2-methyl-7-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidin-4-one; mp 330°-340° C. (dec) after recrystallization from pyridine.

Workup

  1. temperatureis heated at 110°-120° C. for twelve hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe resulting precipitate is filtered
  4. dissolutiondissolved in hot glacial acetic acid
  5. additionactivated charcoal (Darco-G60, Matheson, Coleman and Bell) is added
  6. filtrationthe hot suspension is filtered through Supercell Hyflo® (Johns-Manville)
  7. temperatureThe filtrate is cooled

Sources & evidence

ORD record
ord-6da7c7fad7444810b341a87c7d2b439d
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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