Methyl 4'-(2-aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-carboxylate → 4'-(2-Aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-carboxylic acid

HRID 1524004Notes

Reaction equation

HRID 1524004 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([C:20]([O:22]C)=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:24])=[CH:4][N:3]=1>[OH-].[Na+].C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([C:20]([OH:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:24])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 90312994Methyl 4'-(2-aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 903144344'-(2-Aminopyrimidin-5-yl)-3'-fluoro-[1,1'-biphenyl]-2-carboxylic acidYield 106.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 4′-(2-aminopyrimidin-5-yl)-3′-fluoro-[1,1′-biphenyl]-2-carboxylate (218 mg, 0.67 mmol) in NaOH (8 mL, 2 N) and THF (8 mL) was stirred at 80° Celsius for 48 hours, and then concentrated to dryness. The residue was acidified with 2 N HCl. The precipitate was collected by filtration and washed with water several times, and dried in vacuo to afford the desired product (220 mg, 106%). The crude product was used without further purification. MS (ESI): mass calcd. for C17H12FN3O2, 309.09; m/z found, 309.9 [M+H]+.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water several times
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ab5f42f071fb4b49964b7abf94a372f1
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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