Ethyl 2-methylacetoacetate → HCID 178432490, compound

HRID 1182737Notes

Reaction equation

HRID 1182737 reaction equation
[O-]CC.[Na+].[Na].[CH3:6][CH:7]([C:13](=O)[CH3:14])[C:8]([O:10]CC)=O.Cl.[CH:17]1([C:23](=[NH:25])[NH2:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CCO>[CH:17]1([C:23]2[N:25]=[C:8]([OH:10])[C:7]([CH3:6])=[C:13]([CH3:14])[N:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 701Ethyl 2-methylacetoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21935039Cyclohexanecarboxamidine hydrochloride

Product 1

HCID 178432490HCID 178432490, compoundYield 152.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide (previously prepared by dissolving sodium (6.36 g, 278 mmol, 3 eq) in EtOH (300 ml)), stirring at RT, was treated with ethyl 2-methyl-3-oxobutanoate (16.94 ml, 120 mmol, 1.3 eq). A slurry of cyclohexanecarboximidamide hydrochloride (15 g, 92 mmol, 1 eq) in EtOH (100 ml) was then added and the RM heated at reflux for 8 h. The RM was concentrated, water added and the pH adjusted to ˜7-8 with 2N HCl. Following acidification a white solid precipitated and this was filtered and dried in the vac-oven to yield 2-cyclohexyl-5,6-dimethylpyrimidin-4-ol as a white solid (28.91 g, 151%). 1H (400 MHz, DMSO) 1.03-1.86 (10H, m), 1.96 (3H, s), 2.16 (3H, s), 2.36-2.57 (1H, m), 12.05 (1H, brs); ES+207.

Workup

  1. temperaturethe RM heated
  2. temperatureat reflux for 8 h
  3. concentrationThe RM was concentrated
  4. additionwater added
  5. customprecipitated
  6. filtrationthis was filtered
  7. customdried in the vac-oven

Sources & evidence

ORD record
ord-5aefc0751ffd43c8b61e93b7b328d9d1
Source dataset
uspto-grants-2014_03
Patent number
US08664219B2

Reaction notes

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