1,1'-Carbonyldiimidazole → HCID 178438393, compound

HRID 904524Notes

Reaction equation

HRID 904524 reaction equation
[CH3:1][CH:2]([C:4]1[S:20][C:7]2[N:8]=[C:9]3[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][N:10]3[C:11](=[O:12])[C:6]=2[CH:5]=1)[CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:34][C:35]1[NH:39][N:38]=[N:37][N:36]=1>CN(C)C=O>[CH3:3][CH:2]([C:4]1[S:20][C:7]2[N:8]=[C:9]3[CH:16]=[CH:15][C:14]([C:17]([NH:34][C:35]4[NH:39][N:38]=[N:37][N:36]=4)=[O:18])=[CH:13][N:10]3[C:11](=[O:12])[C:6]=2[CH:5]=1)[CH3:1]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 12862353HCID 12862353, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178438393HCID 178438393, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

2.88 g (0.01 mol) of 2-(1-methylethyl)-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidin-7-carboxylic acid (Example 18) and 3.31 g (0.02 mol) of 1,1' carbonyldiimidazole (Aldrich Chemical Company) in 100 ml of dimethylformamide are stirred and heated in a wax bath at 105° C. for ninety minutes under nitrogen. The mixture is cooled and stirred at room temperature for thirty minutes and 1.03 g (0.01 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company) is added and the resulting mixture is stirred and heated at 105° C. for one hundred thirty-five minutes under nitrogen. The mixture is allowed to stand overnight at room temperature, the precipitate is filtered and the filtrate is evaporated in vacuo. The residue is slurried in boiling methanol, the mixture cooled and filtered. This precipitate is combined with the previous precipitate to give 1.8 g of 2-(1-methylethyl)-4-oxo-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7 -carboxamide; mp 307° C. (dec) after recrystallization from pyridine.

Workup

  1. temperatureThe mixture is cooled
  2. stirringthe resulting mixture is stirred
  3. temperatureheated at 105° C. for one hundred thirty-five minutes under nitrogen
  4. filtrationthe precipitate is filtered
  5. customthe filtrate is evaporated in vacuo
  6. temperaturethe mixture cooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4c083cbce833402c9c6518a8d1859d94
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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