HCID 45256654, compound → HCID 59272362, compound

HRID 1970278Notes

Reaction equation

HRID 1970278 reaction equation
[CH3:1][O:2][C:3]([CH3:32])([CH3:31])[C:4]#[C:5][C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:20]4[CH:21]=[N:22][CH:23]=[N:24][CH:25]=4)=[CH:13][CH:14]=3)[C@@:9]3([CH2:29][O:28][C:27]([NH2:30])=[N:26]3)[C:8]=2[CH:7]=1>CO.[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH3:32])([CH3:31])[CH2:4][CH2:5][C:6]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:20]4[CH:25]=[N:24][CH:23]=[N:22][CH:21]=4)=[CH:13][CH:14]=3)[C@@:9]3([CH2:29][O:28][C:27]([NH2:30])=[N:26]3)[C:8]=2[CH:7]=1

Participants

5

Reactant 1

HCID 45256654HCID 45256654, compound

Product 1

HCID 59272362HCID 59272362, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-2′-(3-methoxy-3-methylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (23 mg, 0.054 mmol) in MeOH (1 mL) suspension of palladium on carbon (28.7 mg, 0.027 mmol) in ethyl acetate (0.5 mL) was added and the mixture was hydrogenated (1 atm) overnight at 40° C. The mixture was cooled to room temperature, filtered through plug of Celite and concentrated to give (R)-2′-(3-methoxy-3-methylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine.

Workup

  1. additionwas added
  2. custom(1 atm) overnight
  3. customat 40° C
  4. filtrationfiltered through plug of Celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65dee49dd4fa4d3ebf14a8b5df944938
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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