Ethanol → HCID 67247986, compound

HRID 335800Notes

Reaction equation

HRID 335800 reaction equation
[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:38]=1)[C:22]1[CH:21]=[C:20]([C:23]3[CH:24]=[N:25][CH:26]=[N:27][CH:28]=3)[CH:19]=CC=1O[C:15]1[C:10]2=[CH:11][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:39].[Na+].[Cl-].O[NH3+].[CH2:44]([OH:46])[CH3:45]>>[C:1]([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:38]=1)[C:10]1[CH:11]=[C:12]([OH:39])[CH:13]=[CH:14][C:15]=1[O:46][C:44]1[C:22]2=[CH:21][C:20]([C:23]2[CH:24]=[N:25][CH:26]=[N:27][CH:28]=2)=[CH:19][CH:45]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21645Hydroxylamine HClHCID 67239736HCID 67239736, compound

Product 1

HCID 67247986HCID 67247986, compound

Procedure

To a mixture of N-tert-butyl-2′-(pyrimidin-5-yl)-7′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine (0.475 g, 0.899 mmol), NaOH solid (0.062 mL, 3.33 mmol), and hydroxyammonium chloride (0.120 mL, 2.88 mmol) was added Ethanol (8 mL). The mixture was stirred at RT. After 48 hrs, the mixture was concentrated in vacuo and the residue partioned between DCM and water. The aqueous layer was acidified to ca. pH=7 and extracted with CH2Cl2. The combined organic fractions were adsorbed onto silica gel and purified by silica gel chromatography using 40-80% Hexanes:EtOAc to give 2-(tert-butylamino)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2′-ol as an off-white solid. MS: MH+=419.2.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionextracted with CH2Cl2
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3be341362c6d49708954449beb11521c
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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