HCID 86731678, compound → HCID 86731679, compound

HRID 1504788Notes

Reaction equation

HRID 1504788 reaction equation
[OH:1][C:2]([CH3:24])([CH3:23])[CH2:3][O:4][CH2:5][C:6]1[N:11]=[C:10]([NH:12]C(=O)OCC2C=CC=CC=2)[CH:9]=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[NH2:12][C:10]1[N:11]=[C:6]([CH2:5][O:4][CH2:3][C:2]([CH3:24])([OH:1])[CH3:23])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 86731678HCID 86731678, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86731679HCID 86731679, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl {6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}carbamate (368 mg, 1.11 mmol) in methanol (11 mL) was added palladium on carbon (10% w/w, 119 mg, 1.11 mmol). A hydrogen balloon was fitted on top of the flask and the flask was evacuated and then backfilled with hydrogen. The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through CELITE, and the CELITE was washed with methanol. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-12% methanol/DCM, linear gradient) to afford 1-[(6-aminopyridin-2-yl)methoxy]-2-methylpropan-2-ol. MS ESI calc'd. for C10H17N2O2 [M+H]+ 197. found 197. 1H NMR (500 MHz, CDCl3) δ 7.42 (t, J=7.8 Hz, 1H), 6.69 (d, J=7.3 Hz, 1H), 6.39 (d, J=8.2 Hz, 1H), 4.53 (s, 2H), 4.49 (s, 1H), 3.41 (s, 2H), 1.23 (s, 6H).

Workup

  1. customthe flask was evacuated
  2. filtrationThe reaction mixture was filtered through CELITE
  3. washthe CELITE was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-12% methanol/DCM, linear gradient)

Sources & evidence

ORD record
ord-bdeea094f7f04a16aaf983d8e82fbea8
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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