Trimethylsilyldiazomethane → Methyl 2-((2,5-dichloropyrimidin-4-yl)amino)benzoate

HRID 2091954Notes

Reaction equation

HRID 2091954 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[C:5]([Cl:18])=[CH:4][N:3]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>C(Cl)Cl.CO.C(OCC)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([O:13][CH3:19])=[O:12])[C:5]([Cl:18])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 715015362-(2,5-Dichloropyrimidin-4-ylamino)benzoic acid

Product 1

HCID 86647794Methyl 2-((2,5-dichloropyrimidin-4-yl)amino)benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-(2,5-dichloropyrimidin-4-ylamino)benzoic acid (300 mg, 1.1 mmol) in DCM/MeOH (10/5 mL) is added trimethylsilyl diazomethane in ethyl ether solution (2.0 M, 2 mL). The mixture is stirred for 30 min and concentrated to afford methyl 2-(2,5-dichloropyrimidin-4-ylamino)benzoate as yellow solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d8a10ade9d9148cd9135202927534141
Source dataset
uspto-grants-2013_05
Patent number
US08440681B2

Reaction notes

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