Benzene → Methyl 2-chloropyrimidine-4-carboxylate

HRID 410428Notes

Reaction equation

HRID 410428 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH:11]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 221357512-Chloropyrimidine-4-carboxylic acid

Product 1

HCID 43811076Methyl 2-chloropyrimidine-4-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloropyrimidine-4-carboxylic acid (1.0 g, 6.31 mmol) in 1:1 benzene (5 mL) and MeOH (5 mL) at 0° C. was added trimethylsilyl-diazomethane (2.0 M solution in hexanes, 3.78 mL, 7.57 mmol) dropwise. The solution was left to stir for 14 hr and concentrated to dryness. Flash chromatography on silica (0-100% EtOAc/hexanes) afforded methyl 2-chloropyrimidine-4-carboxylate (980 mg, 5.68 mmol, 90% yield) as a yellow oil. MS ESI: [M+H]+ m/z 173.0. 1H NMR (500 MHz, CDCl3) δ 8.88 (dd, J=1.5, 4.9, 1H), 7.96 (dd, J=1.5, 4.9, 1H), 4.04 (d, J=1.5, 3H).

Workup

  1. waitThe solution was left
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ab4f329d1e98490983eae4b85979a68c
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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