Ethyl formate → Ethyl 2-methylpyrimidine-5-carboxylate

HRID 1593382Notes

Reaction equation

HRID 1593382 reaction equation
[H-].[Na+].[CH:3]([O:5][CH2:6][CH3:7])=[O:4].C(O[CH:11](OCC)[CH2:12][C:13](OCC)=O)C.Cl.[C:22]([NH2:25])(=[NH:24])[CH3:23]>O.C(O)(=O)C.CCOCC>[CH3:23][C:22]1[N:25]=[CH:11][C:12]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:13][N:24]=1

Participants

8

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 66389Ethyl 3,3-diethoxypropionateHCID 67170Acetamidine monohydrochloride

Product 1

HCID 14639203Ethyl 2-methylpyrimidine-5-carboxylateYield 67.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Into 25 ml of ether was suspended 762 mg of 60% NaH, and then 20 g of ethyl formate was added dropwise under ice-cooling. Then, 12 ml of an ether solution of 5.0 g of ethyl 3.3-diethoxypropanoate was added dropwise thereto. After 2 days of stirring at the same temperature, 2.50 g of acetamidine hydrochloride was added thereto, followed by 1 day of stirring at room temperature. Then, 5 ml of acetic acid and water were added to the reaction solution, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation and the resulting residue was subjected to silica gel column chromatography to obtain 2.93 g of the title compound from an eluate eluted with ethyl acetate-hexane (3:7, v/v).

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-7922cd3362cc47f3b7c57303d928f9bc
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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