Sodium Hydroxide → HCID 59356612, compound

HRID 2192779Notes

Reaction equation

HRID 2192779 reaction equation
[C:1]([C:5]1[NH:6][C:7](=[O:16])[C:8]([C:11]([O:13]CC)=[O:12])=[CH:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:5]1[NH:6][C:7](=[O:16])[C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2304284HCID 2304284, compound

Product 1

HCID 59356612HCID 59356612, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-tert-butyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate (43.9 g) was dissolved in ethanol (200 ml), 2 M aqueous sodium hydroxide solution (330 ml) was added and the mixture was stirred at room temperature for 40 hr. The reaction mixture was concentrated under reduced pressure, and the aqueous layer was adjusted to pH 8 with 6 M hydrochloric acid. The mixture was concentrated under reduced pressure, and subjected to azeotropic distillation with 2-propanol. The residue was suspended in acetone, and insoluble powder was collected by filtration. The obtained powder was suspended in 1 M hydrochloric acid and the suspension was adjusted to pH 3. The suspension was concentrated under reduced pressure. The residue was subjected to azeotropic distillation with 2-propanol, and suspended in acetone. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give the object compound (32.8 g) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThe mixture was concentrated under reduced pressure
  3. distillationsubjected to azeotropic distillation with 2-propanol
  4. filtrationinsoluble powder was collected by filtration
  5. concentrationThe suspension was concentrated under reduced pressure
  6. distillationThe residue was subjected to azeotropic distillation with 2-propanol
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b406494bc394401eaf38a0f4472f84c1
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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