Sodium Hydroxide → HCID 14347507, compound

HRID 2232055Notes

Reaction equation

HRID 2232055 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13]C)=[O:12])[C:6]([CH3:15])=[N:5][C:4]=1[S:16][CH3:17])#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([OH:13])=[O:12])[C:6]([CH3:15])=[N:5][C:4]=1[S:16][CH3:17])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14653240HCID 14653240, compound

Product 1

HCID 14347507HCID 14347507, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a suspension of methyl 5-cyano-1,6-dihydro-2-methyl-4-(methylthio)-6-oxo-1-pyrimidineacetate (2.3 g, 9.0 mmol) in methanol (6 mL) was added 3 N NaOH (3.3 mL, 9.9 mmol). The mixture was warmed to 30° C. for 1.5 hours, then concentrated to remove the methanol. The residue was dissolved in water (20 mL) and neutralized with 3 NHCl (3.3 mL, 9.9 mmol). The resulting precipitate was collected by filtration, and recrystallized from methanol/ether/hexane (twice) to yield pure product (1.5 g, 35%) m.p. 236°-238° C.

Workup

  1. concentrationconcentrated
  2. customto remove the methanol
  3. dissolutionThe residue was dissolved in water (20 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. customrecrystallized from methanol/ether/hexane (twice)

Sources & evidence

ORD record
ord-e8868c3a1b6242aa86f0f2860d4d4fbf
Source dataset
uspto-grants-1988_11
Patent number
US04786638

Reaction notes

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