Chlorotrimethylsilane → HCID 178422238, compound

HRID 1577366Notes

Reaction equation

HRID 1577366 reaction equation
[CH3:1][C:2]1[S:18][C:5]2[N:6]=[C:7]3[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O.[NH2:32][C:33]1[NH:37][N:36]=[N:35][N:34]=1.Cl[Si](C)(C)C.C(N(CC)CC)C.[N-]1C=CN=C1>CN(C)C=O>[CH3:1][C:2]1[S:18][C:5]2[N:6]=[C:7]3[CH:14]=[CH:13][C:12]([C:15]([NH:32][C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[O:17])=[CH:11][N:8]3[C:9](=[O:10])[C:4]=2[CH:3]=1

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 12862350HCID 12862350, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178422238HCID 178422238, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.86 g (0.00715 mol) of 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxylic acid (Example 1) and 1.62 g (0.01 mol) of 1,1'carbonyldiimidazole (Aldrich Chemical Company) in 210 ml of dimethylformamide are stirred at 50° C. for sixteen hours. To 0.83 g (0.008 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company) in 50 ml of dimethylformamide cooled to 0°-5° C. is added 3.0 ml (0.024 mol) of chlorotrimethylsilane (Aldrich Chemical Company) and 6.0 ml (0.043 mol) of triethylamine. After thirty minutes the mixture is allowed to reach room temperature and is stirred for an additional two hours. This mixture is combined with the previous cooled imidazolide mixture and stirred for three days at room temperature. The resulting precipitate is collected, slurried in boiling glacial acetic acid, the mixture is cooled and filtered to give 0.69 g of 2-methyl-4-oxo-N-1H-tetrazol-5-yl-4H-pyrido[1,2 -a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 306°-310° C. (dec).

Workup

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

Sources & evidence

ORD record
ord-db6cedbe7c4145a68f0ee841dd182898
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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