Dimethyl 2,5-pyridine dicarboxylate → HCID 15210653, compound

HRID 1402749Notes

Reaction equation

HRID 1402749 reaction equation
[CH3:1][NH2:2].Cl.C[Al](C)C.[N:8]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][C:9]=1[C:18]([O:20]C)=O>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:1][NH:2][C:18]([C:9]1[N:8]=[CH:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=1)=[O:20]

Participants

6

Reactant 3

HCID 234911Dimethyl 2,5-pyridine dicarboxylateHCID 6364545Methylamine hydrochloride2×HCID 16682925Trimethylaluminum2×

Product 1

HCID 15210653HCID 15210653, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of MeNH2.HCl (173 mg, 5.12 mmol) in toluene (5 mL) at 0° C., was added AlMe3 (2 M solution in Hexanes, 1.28 mL, 2.56 mmol). After 30 minutes the solution was canulated into a stirred solution dimethyl pyridine-2,5-dicarboxylate (500 mg, 2.56 mmol) in DCM (5 mL) at 0° C. before stirring over night at room temperature. An aliquot was taken and analysed by NMR, indicating that there was a 0.8:1 ratio of product to starting material. MeNH2.HCl (173 mg, 5.124 mmol) and AlMe3 (2M solution in Hexanes, 1.28 mL, 2.56 mmol) were added and the reaction stirred for 12 hours. The reaction was quenched by addition of H2O (2 mL) and extracted with EtOAc (2×10 mL). The organics were combined, dried (MgSO4), filtered and concentrated at reduced pressure to give the title compound (520 mg, quant. yield) which was used without further purification.

Workup

  1. stirringthe reaction stirred for 12 hours
  2. customThe reaction was quenched by addition of H2O (2 mL)
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-dba10f2a275e4246aa01b16c559f96f9
Source dataset
uspto-grants-2014_12
Patent number
US08912176B2

Reaction notes

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