Chlorotrimethylsilane → HCID 178522655, compound

HRID 1155869Notes

Reaction equation

HRID 1155869 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12](O)=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[S:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:3]1=2.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1.Cl[Si](C)(C)C.C(N(CC)CC)C.[N-]1C=CN=C1>CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([NH:37][C:38]3[NH:42][N:41]=[N:40][N:39]=3)=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[S:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:17][C:3]1=2

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 128623554-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 178522655HCID 178522655, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.9 g (0.0028 mol) of 4-oxo-2-phenyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid (Example 5) and 0.7 g (0.0043 mol) of 1,1'carbonyldiimidazole (Aldrich Chemical Company) in 80 ml of dimethylformamide are stirred at 60°-70° C. for five hours. To 0.4 g (0.004 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company) in 40 ml of dimethylformamide cooled to 0°-5° C. is added 1.5 ml (0.012 mol) of chlorotrimethylsilane (Aldrich Chemical Company) and 3 ml (0.022 mol) of triethylamine. After thirty minutes the mixture is allowed to reach room temperature and is stirred for an additional 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, and mixture is cooled and filtered to give 0.78 g of 4-oxo-2-phenyl-N-1H-tetrazol-5-yl-4H-pyrido[ 1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 324°-328° C. (dec).

Workup

  1. waitAfter thirty minutes the mixture is allowed
  2. customto reach room temperature
  3. stirringstirred for fourteen hours at room temperature
  4. customThe resulting precipitate is collected
  5. temperatureis cooled
  6. filtrationfiltered

Sources & evidence

ORD record
ord-aa2ea010b73f4200982abb5c1562a910
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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