HCID 22050863, compound → HCID 178428952, compound

HRID 1867001Notes

Reaction equation

HRID 1867001 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[C:10](=[O:35])[N:11]([CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29](C#N)[N:28]=2)[C:12]([CH3:25])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24]>C(O)(C)(C)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Br:8][C:9]1[C:10](=[O:35])[N:11]([CH2:26][C:27]2[CH:32]=[CH:31][N:30]=[C:29]([OH:4])[N:28]=2)[C:12]([CH3:25])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24]

Participants

3

Reactant 1

HCID 22050863HCID 22050863, compound

Product 1

HCID 178428952HCID 178428952, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-{[3-Bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]methyl}pyrimidine-2-carbonitrile trifluoroacetate (0.2 g, 0.00035 mol) potassium fluoride on aluminum oxide (0.25 g) in t-butanol (5.0 mL) was refluxed for 4 h under argon atmosphere. The reaction mixture was cooled, filtered the precipitate and washed with ethanol. The combined filtrate and washings were concentrated to dryness and the residue was purified by reverse-phase HPLC using 10-90% acetonitrile/water gradient (30 min) at a flow rate of 100 mL/min. The appropriate fractions (m/z=452) were combined and freeze dried to afford the title compound (0.05 g) as a white powder:

Workup

  1. temperaturewas refluxed for 4 h under argon atmosphere
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered the precipitate
  4. washwashed with ethanol
  5. concentrationThe combined filtrate and washings were concentrated to dryness
  6. customthe residue was purified by reverse-phase
  7. custom10-90% acetonitrile/water gradient (30 min)
  8. customfreeze dried

Sources & evidence

ORD record
ord-e4befb2e8f274d30bea13fe56e4e31ee
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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