Ethyl 2-methylacetoacetate → HCID 178432484, compound

HRID 1896186Notes

Reaction equation

HRID 1896186 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[NH:6])[NH2:5].C(N(CC)CC)C.[CH3:18][CH:19]([C:25](=O)[CH3:26])[C:20](OCC)=[O:21]>C(O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]1[N:5]=[C:20]([OH:21])[C:19]([CH3:18])=[C:25]([CH3:26])[N:6]=1

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 8471TriethylamineHCID 27409182-Chlorobenzimidamide

Product 1

HCID 178432484HCID 178432484, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 2-chlorobenzimidamide (34.07 g, 220 mmol) and triethylamine (44.50 g, 440 mmol) in ethanol (750 mL) was added ethyl 2-methyl-3-oxobutanoate (38.13 g, 264 mmol). The reaction was heated at 90° C. for 4 h. A further portion (6.36 g) of the ester was added and the reaction was stirred for 3 h. The reaction was concentrated to around 500 mL and stood overnight. Precipitation of the desired pyrimidinol (22.7 g) occurred. The mother liquors were concentrated and DCM and 1M HCl were added. The aqueous layer was extracted 7 times with DCM to give further crops of the desired product (total: 28.9 g, 56%) on concentration as a white solid.

Workup

  1. concentrationThe reaction was concentrated to around 500 mL
  2. waitstood overnight
  3. customPrecipitation of the desired pyrimidinol (22.7 g)
  4. concentrationThe mother liquors were concentrated
  5. additionDCM and 1M HCl were added
  6. extractionThe aqueous layer was extracted 7 times with DCM

Sources & evidence

ORD record
ord-9d88008aa5254771b913736308c0a8d5
Source dataset
uspto-grants-2013_08
Patent number
US08518953B2

Reaction notes

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