Methane → HCID 178435054, compound

HRID 1577408Notes

Reaction equation

HRID 1577408 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:18])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]1[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:7]1=[N:6]2.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].C>CN(C)C=O.N1C=CC=CC=1>[CH3:1][C:2]1[S:3][C:4]([CH3:18])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]1[CH:12]=[C:13]([C:16]3[NH:21][N:20]=[N:19][N:17]=3)[CH:14]=[CH:15][C:7]1=[N:6]2

Participants

7

Reactant 4

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12953064HCID 12953064, compound

Product 1

HCID 178435054HCID 178435054, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4.4 g (0.0172 mol) of 1,3-dimethyl-10-oxo-10H-pyrido-[1,2-a]thieno[3,4-d]pyrimidine-7-carbonitrile (Example 51), 6.5 g (0.1 mol) of sodium azide and 5.3 g (0.1 mol) of ammonium chloride in 180 ml of dimethylformamide is stirred and heated in a wax bath at 120° C. for seventeen hours under nitrogen. The reaction mixture is cooled, filtered and the filtrate evaporated. The residue is treated with 250 ml of water and acidified with concentrated hydrochloric acid. This mixture is warmed on a steam bath, cooled and filtered to give 5.1 g of crude product. This material is dissolved in hot pyridine, activated charcoal (Darco-G60, Matheson, Coleman and Bell) is added and the hot suspension is filtered through Supercell Hyflo® (Johns-Mansville). The filtrate is cooled to give 3.1 g of 1,3-dimethyl-7-(1H-tetrazol-5-yl)-10H-pyrido[1,2-a]thieno-[3,4-d]pyrimidin-10-one; mp 292° C. (dec).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. additionThe residue is treated with 250 ml of water
  5. temperatureThis mixture is warmed on a steam bath
  6. temperaturecooled
  7. filtrationfiltered
  8. customto give 5.1 g of crude product
  9. filtrationthe hot suspension is filtered through Supercell Hyflo® (Johns-Mansville)
  10. temperatureThe filtrate is cooled

Sources & evidence

ORD record
ord-9b49323b3fb2477bae24c7a58afae0dc
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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