Chlorotrimethylsilane → HCID 178435418, compound

HRID 1155866Notes

Reaction equation

HRID 1155866 reaction equation
[CH2:1]([C:3]1[S:19][C:6]2[N:7]=[C:8]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][N:9]3[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:33][C:34]1[NH:38][N:37]=[N:36][N:35]=1.Cl[Si](C)(C)C.C(N(CC)CC)C.[N-]1C=CN=C1>CN(C)C=O>[CH2:1]([C:3]1[S:19][C:6]2[N:7]=[C:8]3[CH:15]=[CH:14][C:13]([C:16]([NH:33][C:34]4[NH:38][N:37]=[N:36][N:35]=4)=[O:18])=[CH:12][N:9]3[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 12862351HCID 12862351, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178435418HCID 178435418, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.64 g (0.0023 mol) of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid (Example 2) and 0.75 g (0.0046 mol) of 1,1'carbonyldiimidazole (Aldrich Chemical Company) in 70 ml of dimethylformamide are stirred at 70° C. for two and one-half hours. To 0.31 g (0.003 mol) of 5-amino-tetrazole monohydrate (Aldrich Chemical Company) in 40 ml of dimethyl/formamide cooled to 0°-5° C. is added 1.5 ml (0.012 mol) of chlorotrimethylsilane (Aldrich Chemical Company) and 2.5 ml (0.018 mol) of triethylamine. The mixture is stirred and allowed to reach room temperature. After two hours the mixture is combined with the previous imidazolide mixture and stirred for fourteen hours at room temperature. The resulting precipitate is collected, slurried in boiling glacial acetic acid, the mixture is cooled and filtered to give 0.58 g of 2-ethyl-4-oxo-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d] pyrimidine-7-carboxamide; mp 310°-312° C. (dec).

Workup

  1. customto reach room temperature
  2. stirringstirred for fourteen hours at room temperature
  3. customThe resulting precipitate is collected
  4. temperaturethe mixture is cooled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b7398f35c5304b639a6e1b14423c7ce2
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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