Sodium Hydroxide → HCID 59356612, compound

HRID 1509541Notes

Reaction equation

HRID 1509541 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), 2M 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 aqueous layer of the mixture was adjusted to pH 8 with 6M hydrochloric acid. The mixture was concentrated under reduced pressure and azeotroped with 2-propanol. The residue was suspended in acetone, and insoluble powder was collected by filtration. The obtained powder was suspended in 1M hydrochloric acid and the mixture was adjusted to pH 3, and concentrated under reduced pressure. The residue was azeotroped with 2-propanol, and the insoluble material was suspended in acetone and filtered off. The filtrate was concentrated under reduced pressure to give the object product (32.8 g) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and aqueous layer of the mixture
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customazeotroped with 2-propanol
  4. filtrationinsoluble powder was collected by filtration
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was azeotroped with 2-propanol
  7. filtrationfiltered off
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f94feaacb7144d79160931ea5edb969
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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