HCID 67460719, compound → HCID 178525222, compound

HRID 1470318Notes

Reaction equation

HRID 1470318 reaction equation
C([O:8][C:9]1[C:14]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][N:12]=[C:11]([N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)[N:10]=1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[C:14]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][N:12]=[C:11]([N:19]2[CH:23]=[CH:22][CH:21]=[N:20]2)[N:10]=1

Participants

4

Reactant 1

HCID 67460719HCID 67460719, compound2×

Product 1

HCID 178525222HCID 178525222, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidin-5-yl)acetic acid, 12-c, (1.239 g, 4 mmol) in THF (40 ml) was added Pd(OH)2/C (0.14 g). The resulting mixture was hydrogenated at room temperature at 1 atm overnight. The mixture was filtered and the filtrate was concentrate under vacuum to give compound 12-d (800 mg, 91%). 1H NMR (DMSO-d6, 300 MHz): δ 12.59 (s, 2H), 8.53 (s, 1H), 7.89 (s, 2H), 6.61 (s, 1H), 3.37 (s, 2H). (M+H)+=221.1.

Workup

  1. customwas hydrogenated at room temperature at 1 atm overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrate under vacuum
  4. customto give compound 12-d (800 mg, 91%)

Sources & evidence

ORD record
ord-a7dee8d87574446099429b496d92e167
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

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