Methyl pivaloylacetate → HCID 178441204, compound

HRID 617781

Reaction equation

HRID 617781 reaction equation
[CH3:1][C:2]([CH3:11])([CH3:10])[C:3](=O)[CH2:4][C:5](OC)=[O:6].C(=O)(O)O.[NH2:16][C:17]([NH2:19])=[NH:18]>C(O)C>[NH2:19][C:17]1[N:18]=[C:5]([OH:6])[CH:4]=[C:3]([C:2]([CH3:11])([CH3:10])[CH3:1])[N:16]=1

Participants

4

Reactant 2

HCID 99597Methyl pivaloylacetateHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 178441204HCID 178441204, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4,4-dimethyl-3-oxopentanoate (15.82 g) and guanidine carbonate (20.0 g) were mixed in 80 mL of ethanol, and the solution refluxed for 16 hours. The reaction mixture was concentrated to 50 mL by removal of solvent under reduced pressure, and 20 mL of water was added. The remaining mixture was acidified to pH 5 with acetic acid, affording a white precipitate. The precipitate was collected by filtration, washed with water, and dried in a vacuum oven to give 2-amino-4-hydroxy-6-tert-butylpyrimidine (12.6 g), m.p. 285-288° C. (dec.).

Workup

  1. temperaturethe solution refluxed for 16 hours
  2. concentrationThe reaction mixture was concentrated to 50 mL by removal of solvent under reduced pressure, and 20 mL of water
  3. additionwas added
  4. customaffording a white precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3935bcc626be4458859a6021f564f99f
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Linked notes

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