Sodium Hydroxide → HCID 89873398, compound

HRID 626460Notes

Reaction equation

HRID 626460 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[NH:9][C:10](=[O:19])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8]2[NH:9][C:10](=[O:19])[C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 89873329HCID 89873329, compound

Product 1

HCID 89873398HCID 89873398, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-((1,1′-biphenyl)-4-ylamino)-6-oxo-1,6-dihydropyrimidine-5-carboxylate (100 mg, 0.298 mmol), sodium hydroxide (1M, aq), and methanol was stirred at 70° C. for 2 hours and for 40° C. overnight. The ester did not dissolve in 3 mL methanol. The ester was then put in 3 mL dioxane and heated to 103° C. for 4 hours with an additional 1 mL of NaOH added. The reaction mixture was then heated at 40° C. overnight. After the overnight heating, the reaction mixture was cooled and the solvent removed. The reaction mixture was diluted with water, and the pH was adjusted to about 3.0. The reaction mixture was filtered to obtain the end product. 1H-NMR confirmed the product (55 mg, 60.0% yield).

Workup

  1. additionadded
  2. temperatureThe reaction mixture was then heated at 40° C. overnight
  3. temperatureAfter the overnight heating
  4. temperaturethe reaction mixture was cooled
  5. customthe solvent removed
  6. additionThe reaction mixture was diluted with water
  7. filtrationThe reaction mixture was filtered
  8. customto obtain the end product

Sources & evidence

ORD record
ord-0e34f434b7f94c2484f78f33a47d5b14
Source dataset
uspto-grants-2016_04
Patent number
US09309232B2

Reaction notes

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