Methanol → HCID 58466281, compound

HRID 335724Notes

Reaction equation

HRID 335724 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:7][C:6]([C:8]2[CH:21]=[CH:20][C:19]3[O:18][C:17]4[C:12](=[CH:13][C:14]([C:22]5[CH:23]=[N:24][CH:25]=[N:26][CH:27]=5)=[CH:15][CH:16]=4)[C@@:11]4([CH2:31][O:30][C:29]([NH2:32])=[N:28]4)[C:10]=3[CH:9]=2)=[CH:5][CH2:4][O:3]1.CO.[H][H]>[Pd]>[CH3:1][C:2]1([CH3:33])[CH2:7][CH:6]([C:8]2[CH:21]=[CH:20][C:19]3[O:18][C:17]4[C:12](=[CH:13][C:14]([C:22]5[CH:27]=[N:26][CH:25]=[N:24][CH:23]=5)=[CH:15][CH:16]=4)[C@@:11]4([CH2:31][O:30][C:29]([NH2:32])=[N:28]4)[C:10]=3[CH:9]=2)[CH2:5][CH2:4][O:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 67241278HCID 67241278, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58466281HCID 58466281, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (R)-2′-(2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (55 mg, 0.125 mmol) in MeOH (2 mL) palladium on carbon (66.4 mg, 0.062 mmol) was added and the mixture was hydrogenated at 50° C. (1 atm of hydrogen gas) for 30 min. Another 20 mg of Pd/C was added and hydrogenation was continued for 1.5 hr at 50° C. The mixture was filtered through a plug of celite and purified by silica gel chromatography (10-80% DCM/MeOH/NH4OH in DCM) to afford (R)-2′-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine.

Workup

  1. customwas hydrogenated at 50° C.
  2. customfor 30 min
  3. filtrationThe mixture was filtered through a plug of celite
  4. custompurified by silica gel chromatography (10-80% DCM/MeOH/NH4OH in DCM)

Sources & evidence

ORD record
ord-6622d32a070643109c074ca21b14076a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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