Ethyl Acetoacetate → Ethyl 6-methyl-4-(2-nitrophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524561Notes

Reaction equation

HRID 524561 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].Cl.[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18](=[NH:20])[NH2:19].O=[C:22]([CH3:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])(=O)C.[Na+]>C(O)C>[CH3:29][C:22]1[NH:19][C:18]([C:14]2[S:13][CH:17]=[CH:16][N:15]=2)=[N:20][CH:6]([C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 111012-NitrobenzaldehydeHCID 517045Sodium AcetateHCID 186795841,3-Thiazole-2-carboximidamide hydrochloride

Product 1

HCID 118107568Ethyl 6-methyl-4-(2-nitrophenyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 48.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
88 °C

Procedure

A mixture of 2-nitrobenzaldehyde (10 g, 66 mmol), thiazole-2-carboximidamide hydrochloride (10.8 g, 66 mmol), ethyl 3-oxobutanoate (8.6 g, 66 mmol) and sodium acetate (5.5 g, 66 mmol) in ethanol (250 mL) was stirred at 88° C. for 16 hours, then cooled to 25° C. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as a light yellow solid (12 g, 48%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperaturecooled to 25° C
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1)

Sources & evidence

ORD record
ord-b34fa246cf4e48ed8af8fa355f830386
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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