Chlorotrimethylsilane → HCID 178435030, compound

HRID 1577371Notes

Reaction equation

HRID 1577371 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[C:3]=1[CH3:19].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>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:33][C:34]4[NH:38][N:37]=[N:36][N:35]=4)=[O:17])=[CH:11][N:8]3[C:9](=[O:10])[C:4]=2[C:3]=1[CH3:19]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 12862356HCID 12862356, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178435030HCID 178435030, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

From 1 g (0.0036 mol) of 2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]-thieno[2,3-d]pyrimidine-7-carboxylic acid (Example 6), 0.83 g (0.0051 mol) of 1,1'carbonyldiimidazole (Aldrich Chemical Company) in 50 ml of dimethylformamide and 0.41 g (0.004 mol) of 5-aminotetrazole monohydrate (Aldrich Chemical Company), 1.5 ml (0.012 mol) of chlorotrimethylsilane (Aldrich Chemical Company), 3.0 ml (0.022 mol) of triethylamine in 40 ml of dimethylformamide, following the procedure of Example 11, there is obtained 0.73 g of 2,3-dimethyl-4-oxo-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno-[2,3-d]pyrimidine-7-carboxamide after slurrying in boiling glacial acetic acid, cooling and filtering the precipitate; mp 297°-300° C. (dec).

Sources & evidence

ORD record
ord-df042f2470094cd381fe50751fb1167b
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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