Sodium Hydroxide → 3-[5-Bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid

HRID 2172591Notes

Reaction equation

HRID 2172591 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Br:18])=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[N:13]=[C:12]2[CH3:29])[CH:5]=1.[OH-].[Na+]>O1CCCC1>[Br:18][C:15]1[C:16](=[O:17])[N:11]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=2[CH3:10])[C:3]([OH:30])=[O:2])[C:12]([CH3:29])=[N:13][C:14]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21089021Methyl 3-[5-bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate

Product 1

HCID 210892453-[5-Bromo-4-[(2,4-difluorobenzyl)oxy]-2-methyl-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[5-bromo-4-(2,4-difluoro-benzyloxy)-2-methyl-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester from Step B (50 mg, 1.04 mmol) in tetrahydrofuran (3 mL) was added 1N sodium hydroxide (2 mL) and the solution was stirred at ambient temperature for four hours. The solution was concentrated in vacuo and the aqueous residue was acidified to pH=2 using 1M HCl. The solution was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The slurry was filtered and concentrated to a light yellow semi-solid (470 mg, 97%). MS (M, M+2): 465, 467

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. extractionThe solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated to a light yellow semi-solid (470 mg, 97%)

Sources & evidence

ORD record
ord-adb946842c1345fdb6a1ef4c58104f24
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

Loading…