Dimethyl malonate → HCID 86642125, compound

HRID 885949Notes

Reaction equation

HRID 885949 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[C:15]([CH3:20])[N:14]=1>C1COCC1>[CH3:6][O:5][C:3](=[O:4])[CH:2]([C:17]1[CH:18]=[C:13]([Cl:12])[N:14]=[C:15]([CH3:20])[N:16]=1)[C:1]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 2349974,6-Dichloro-2-methylpyrimidine

Product 1

HCID 86642125HCID 86642125, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl malonate (0.39 mL, 3.37 mmol) in THF (20 mL) was added sodium hydride (60% dispersion in oil, 138 mg, 3.37 mmol) portionwise. The reaction mixture was stirred for 10 minutes at r.t. then 4,6-dichloro-2-methylpyrimidine (500 mg, 3.07 mmol) was added and the mixture heated to reflux for 2 h. The resulting suspension was concentrated in vacuo, triturated with Et2O (3×30 mL) and the mother liquors were evaporated in vacuo to yield the title compound (300 mg, 40%) as an off-white solid. LCMS (ES+) 259.0 (M+H)+, RT 2.93 minutes (90% purity) (Method 2).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 h
  3. concentrationThe resulting suspension was concentrated in vacuo
  4. customtriturated with Et2O (3×30 mL)
  5. customthe mother liquors were evaporated in vacuo

Sources & evidence

ORD record
ord-eae703e4842544b38700ed9d50b35bd7
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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