Hydrochloric Acid → HCID 178514882, compound

HRID 904541Notes

Reaction equation

HRID 904541 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[S:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:16][C:3]1=2.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[C:17]1([C:15]2[S:14][C:4]3[N:5]=[C:6]4[CH:11]=[CH:10][C:9]([C:12]5[NH:25][N:24]=[N:23][N:13]=5)=[CH:8][N:7]4[C:2](=[O:1])[C:3]=3[CH:16]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 128623744-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carbonitrile

Product 1

HCID 178514882HCID 178514882, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (0.005 mol) of 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carbonitrile (Example 31), 1.0 g (0.0153 mol) of sodium azide and 0.9 g (0.0168 mol) of ammonium chloride in 200 ml of dimethylformamide is heated at 110°-120° C. for three days. 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 pyridine, 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 0.55 g of 2-phenyl-7-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidin-4-one; mp 310°-312° C. (dec) after recrystallization from pyridine.

Workup

  1. temperatureis heated at 110°-120° C. for three days
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe resulting precipitate is filtered
  4. dissolutiondissolved in hot pyridine
  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-b53b1898b856429a94e64696ed58acae
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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