Tert-butyl 2-(2,4-dichlorobenzylidene)-3-oxobutanoate → 6-Tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate

HRID 1868456Notes

Reaction equation

HRID 1868456 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[Cl:12][C:13]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:14]=1[CH:15]=[C:16]([C:24](=O)[CH3:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(O)C>[Cl:12][C:13]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:14]=1[CH:15]1[N:3]2[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]2[NH:1][C:24]([CH3:25])=[C:16]1[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18].[Cl:12][C:13]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:14]=1[CH:15]1[N:6]2[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][N:3]=[C:2]2[NH:1][C:24]([CH3:25])=[C:16]1[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18]

Participants

5

Reactant 2

HCID 67021125Tert-butyl 2-(2,4-dichlorobenzylidene)-3-oxobutanoateHCID 178469899HCID 178469899, compound

Product 2

HCID 469017426-Tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylateHCID 469020386-Tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylateYield 212.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl 2-amino-1H-imidazole-4-carboxylate (980 mg, 6.8 mmol) and tert-butyl 2-(2,4-dichlorobenzylidene)-3-oxobutanoate (2.03 g, 6.4 mmol) were dissolved in ethanol (15 mL) and the reaction was heated to 75° C. for 16 h. The reaction was concentrated under reduced pressure to obtain a 10:1 mixture (by HPLC) of 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate and 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate (3.07 g, 100% crude yield) as a yellow foam. A small amount of this mixture (350 mg) was purified by silica gel chromatography to obtain 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (190 mg, 54%) and 6-tert-butyl 3-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-3,6-dicarboxylate (19 mg, 5.4%) as white solids.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27c63ab4919b46be9a6133abc24e85d7
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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