HCID 67283015, compound → HCID 67281494, compound

HRID 913039Notes

Reaction equation

HRID 913039 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([O:21][CH3:22])[C:17]([F:20])([F:19])[F:18])=[CH:12][NH:11][C:10]=1[CH3:23])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]([O:21][CH3:22])[C:17]([F:18])([F:19])[F:20])=[CH:12][NH:11][C:10]=1[CH3:23]

Participants

4

Reactant 1

HCID 67283015HCID 67283015, compound

Product 1

HCID 67281494HCID 67281494, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A clear solution of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-methoxy-ethyl)-1H-pyridin-4-one (609 mg, 1.86 mmol) in methanol (32 mL) was debenzylated using Pd/C (10 wt. %, dry basis, on activated carbon, wet, Degussa type E101 NE/W, 154 mg) as catalyst under a hydrogen atmosphere at 50 psi of pressure. The reaction was completed in 55 min. The mixture was diluted with methanol (50 mL), sonicated for 10 min. A CELITE™ bed was prepared on a sintered glass, and washed with 6M HCl (100 mL), followed by water (7×50 mL) and then methanol (2×50 mL) under suction. The reaction mixture was filtered through the pre-treated CELITE™ bed. The filtrate was collected and concentrated in vacuo to give 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-methoxy-ethyl)-1H-pyridin-4-one as a solid product (0.27 g, 61% yield, HPLC Method 1 (Example 24), RT=9.7 min, purity (peak percent area): 99.3% at λ=280 nm). 1H NMR (DMSO-d6) δ ppm: 7.42 (s, 1H), 5.19 (q, J=7.0 Hz, 1H), 3.32 (s, 3H), 2.20 (s, 3H); MS-ESI (m/z) 238.1 [M+1]+, 206.2 (100%), 186.1, 178.2, 158.2.

Workup

  1. customsonicated for 10 min
  2. customA CELITE™ bed was prepared on a sintered glass
  3. washwashed with 6M HCl (100 mL)
  4. filtrationThe reaction mixture was filtered through the pre-treated CELITE™ bed
  5. customThe filtrate was collected
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b577eb5849940a88b4685b057d21f2b
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

Loading…