Trimethylsilyldiazomethane → HCID 118598713, compound

HRID 1050385Notes

Reaction equation

HRID 1050385 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[S:15])[NH:13][C:12]([C:16]([OH:18])=[O:17])=[C:11]([CH3:19])[CH:10]=2)[CH:3]=1.[CH3:20][Si](C=[N+]=[N-])(C)C>O1CCCC1.CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[C:14](=[S:15])[NH:13][C:12]([C:16]([O:18][CH3:20])=[O:17])=[C:11]([CH3:19])[CH:10]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 118598626HCID 118598626, compound

Product 1

HCID 118598713HCID 118598713, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-((6-aminopyrimidin-4-yl)amino)-3-methyl-6-thioxo-1,6-dihydropyridine-2-carboxylic acid (5, 0.5 g, 1.72 mmol) in tetrahydrofuran (10 mL) and methanol is added (trimethylsilyl)diazomethane (2 M in hexanes, 1.29 mL, 2.58 mmol). The reaction is stirred at room temperature for 1 h. The resulting mixture is concentrated and purified via column chromatography to afford methyl 5-(6-aminopyrimidin-4-yl)amino)-3-methyl-6-thioxo-1,6-dihydropyridine-2-carboxylate (6).

Workup

  1. concentrationThe resulting mixture is concentrated
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-906e36439e27478b95cc2c883b34485b
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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