Sodium Hydroxide → 4-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid

HRID 928266

Reaction equation

HRID 928266 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[C:9]([NH:10][C:11]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[N:14]=[C:13]([C:21]3[CH:26]=[C:25]([Br:27])[CH:24]=[CH:23][C:22]=3[F:28])[N:12]=2)=[CH:8][CH:7]=[N:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[Br:27][C:25]1[CH:24]=[CH:23][C:22]([F:28])=[C:21]([C:13]2[N:12]=[C:11]([NH:10][C:9]3[C:4]([C:3]([OH:29])=[O:2])=[CH:5][N:6]=[CH:7][CH:8]=3)[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[N:14]=2)[CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 577423794-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic Acid Methyl Ester

Product 1

HCID 577423744-[[2-(5-Bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic AcidYield 82.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 4-[[2-(5-bromo-2-fluorophenyl)pteridin-4-yl]amino]nicotinic acid methyl ester 107 (200 mg, 0.439 mmol) and NaOH (44 mg, 1.10 mmol) in THF/MeOH/H2O (3:2:1, 5 mL), was stirred at room temperature for 3 h. The solvent was evaporated, and the residue dissolved in H2O, neutralized with AcOH, filtered off, and successively washed with H2O, MeOH and Ether to give 160 mg of the title product 16 as a yellow powder (LCMS analysis).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in H2O
  3. filtrationfiltered off
  4. washsuccessively washed with H2O, MeOH and Ether

Sources & evidence

ORD record
ord-736403cc896f4faca428dd875149340e
Source dataset
uspto-grants-2016_03
Patent number
US09290502B2

Linked notes

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