Chlorotrimethylsilane → HCID 178438394, compound

HRID 1155867Notes

Reaction equation

HRID 1155867 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([OH:14])=O)[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[S:15][C:16]([CH2:18][CH2:19][CH3:20])=[CH:17][C:3]1=2.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:34][C:35]1[NH:39][N:38]=[N:37][N:36]=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:34][C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[O:14])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[S:15][C:16]([CH2:18][CH2:19][CH3:20])=[CH:17][C:3]1=2

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 12862352HCID 12862352, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178438394HCID 178438394, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.77 g (0.02 mol) of 4-oxo-2-propyl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid (Example 3) and 6.49 g (0.04 mol) of 1,1'carbonyldiimidazole (Aldrich Chemical Company) in 100 ml of dimethylformamide are stirred at 50° C. for one hour. To 2.5 g (0.024 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company) in 50 ml of dimethylformamide cooled to 0°-5° C. is added 9.14 ml (0.072 mol) of chlorotrimethylsilane (Aldrich Chemical Company) and 10 ml (0.072 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 0.9 g, of 4-oxo-2-propyl-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide is collected; mp 306°-308° C. (dec) after recrystallization from pyridine.

Workup

  1. customto reach room temperature
  2. stirringstirred for fourteen hours at room temperature
  3. customThe resulting precipitate 0.9 g, of 4-oxo-2-propyl-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide is collected
  4. custommp 306°-308° C. (dec) after recrystallization from pyridine

Sources & evidence

ORD record
ord-c491becc6d1648d1be334881bc2c3433
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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