Hydrochloric Acid → HCID 178422236, compound

HRID 1155887Notes

Reaction equation

HRID 1155887 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 11 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-bba95ff01cc34cf28cb5be31c11e8311
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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