HCID 45256823, compound → HCID 45256296, compound

HRID 1970416Notes

Reaction equation

HRID 1970416 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[C:3]#[C:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C@@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1>[Pd].C(O)C>[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[N:23][CH:24]=4)=[CH:12][CH:13]=3)[C@@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1

Participants

4

Reactant 1

HCID 45256823HCID 45256823, compound

Product 1

HCID 45256296HCID 45256296, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (400 mg, 0.974 mmol) and palladium on carbon (104 mg, 0.974 mmol) were combined in 20 ml of ethanol and stirred under an atmosphere of hydrogen for 12 hours. The solution is filtered thru celite and concentrated. The product is purified via silica gel column chromatography (RediSep 80 g column) using 0-10% methanol in ethyl acetate to afford (R)-2′-(3,3-dimethylbutyl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white crystalline solid. Found MS: MH+=415.2.

Workup

  1. filtrationThe solution is filtered thru celite
  2. concentrationconcentrated
  3. customThe product is purified via silica gel column chromatography (RediSep 80 g column)

Sources & evidence

ORD record
ord-911753133d334b67b8c92d1414c95bb1
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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