Acetonitrile → Ethyl 7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylate

HRID 2359714Notes

Reaction equation

HRID 2359714 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.C1CCN2C(=NCCC2)CC1.C(#N)C>ClCCl.O>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:22]=1)[C:11](=[O:13])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:23]=2

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6871Diethyl (ethoxymethylene)malonateHCID 153482-Amino-5-methylpyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 228526Ethyl 7-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of diethyl 2-(ethoxymethylene)malonate (0.60 g, 3 mmol), 5-methylpyridin-2-amine (0.20 g, 2 mmol), DBU (0.1 ml, 0.9 mmol) in acetonitrile (2 g, 49 mmol) was heated under Microwave (CEM) at 150° C. (150 W) for 20 min. The resultant was diluted with dichloromethane and water, and the organic layer was dried over sodium sulfate. The organic solution was concentrated, and the residue was crystallized in dichloromethane and diethyl ether to give the title compound as a pale yellow solid (0.25 g, 58%): MS (ESI pos. ion) m/z: 233 (MH+). Calc'd exact mass for C12H12N2O3: 232.

Workup

  1. dry with materialthe organic layer was dried over sodium sulfate
  2. concentrationThe organic solution was concentrated
  3. customthe residue was crystallized in dichloromethane

Sources & evidence

ORD record
ord-3e36e65b0eb54dd7b5cb5bf055060c57
Source dataset
uspto-grants-2014_04
Patent number
US08685983B2

Reaction notes

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