1,1'-Carbonyldiimidazole → HCID 178435055, compound

HRID 1155904Notes

Reaction equation

HRID 1155904 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:19])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]1[CH:12]=[C:13]([C:16]([OH:18])=O)[CH:14]=[CH:15][C:7]1=[N:6]2.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:33][C:34]1[NH:38][N:37]=[N:36][N:35]=1>CN(C)C=O>[CH3:1][C:2]1[S:3][C:4]([CH3:19])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]1[CH:12]=[C:13]([C:16]([NH:33][C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[O:18])[CH:14]=[CH:15][C:7]1=[N:6]2

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 12953061HCID 12953061, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178435055HCID 178435055, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.6 g (0.0022 mol) of 1,3-dimethyl-10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid (Example 48) and 0.84 g (0.005 mol) of 1,1' carbonyldiimidazole (Aldrich Chemical Company) in 90 ml of dimethylformamide is stirred and heated in a wax bath in 105° C. for eighty five minutes under nitrogen. The mixture is allowed to stand at room temperature for thirty minutes and then 0.225 g (0.0022 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company) is added and the mixture heated at 105° C. for three and one-half hours. The solvent is evaporated and the residue suspended in hot methanol, cooled and 0.71 g of crude product is collected. 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-Manville). The filtrate is cooled to give 0.47 g of 1,3-dimethyl-10-oxo-N-1H-tetrazol-5-yl-10 H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxamide with pyridine (1:0.2); mp>300° C. (dec).

Workup

  1. waitto stand at room temperature for thirty minutes
  2. temperaturethe mixture heated at 105° C. for three and one-half hours
  3. customThe solvent is evaporated
  4. temperaturecooled
  5. custom0.71 g of crude product is collected
  6. dissolutionThis material is dissolved in hot pyridine
  7. additionactivated charcoal (Darco G60, Matheson, Coleman and Bell) is added
  8. filtrationthe hot suspension is filtered through Supercell Hyflo® (Johns-Manville)
  9. temperatureThe filtrate is cooled

Sources & evidence

ORD record
ord-420d02d9b8eb4530885021ed5db613e3
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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