Trimethylsilyldiazomethane → Methyl 2-chloropyrimidine-5-carboxylate

HRID 2093618Notes

Reaction equation

HRID 2093618 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[CH3:11][O:9][C:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[N:7][CH:6]=1)=[O:10]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 110949062-Chloropyrimidine-5-carboxylic acid

Product 1

HCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution 2-chloropyrimidine-5-carboxylic acid (1.63 g, 10.28 mmol) in a mixture of methanol (20 ml) and benzene (50 ml) was added a solution of (trimethylsilyl)diazomethane in hexanes (2.0 M, 10 ml) at room temperature. The mixture was stirred for 30 min, and then was concentrated to give the title compound (1.77 g) as a yellow solid. Mass spectrum (ESI) 173.2 (M+1). 1H NMR (500 MHz, CDCl3) δ 9.18 (s, 2H), 4.02 (s, 3H).

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-f2b8cd3c6c554656b7987b188d8bf86b
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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