tert-Butyl hydroperoxide → HCID 68283482, compound

HRID 1855307Notes

Reaction equation

HRID 1855307 reaction equation
C(OO)(C)(C)C.[OH-].[NH4+:8].[Br:9][C:10]1[CH:23]=[C:22]2[C:13]([O:14][C:15]3[C:16]([F:35])=[CH:17][C:18]([O:33][CH3:34])=[CH:19][C:20]=3[C:21]32[C:27]2=[N:28][CH2:29][CH2:30][CH2:31][N:26]2[C:25](=S)[NH:24]3)=[CH:12][CH:11]=1>CO>[Br:9][C:10]1[CH:23]=[C:22]2[C:13]([O:14][C:15]3[C:16]([F:35])=[CH:17][C:18]([O:33][CH3:34])=[CH:19][C:20]=3[C:21]32[C:27]2=[N:28][CH2:29][CH2:30][CH2:31][N:26]2[C:25]([NH2:8])=[N:24]3)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14923Ammonium HydroxideHCID 86710012HCID 86710012, compound

Product 1

HCID 68283482HCID 68283482, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl hydroperoxide (70% in water) (1.945 mL, 20.08 mmol), ammonium hydroxide (13.03 mL, 335 mmol), and 7′-bromo-4′-fluoro-2′-methoxy-3,4-dihydro-2H-spiro[imidazo[1,5-a]pyrimidine-8,9′-xanthene]-6(7H)-thione (300 mg, 0.669 mmol) were combined in MeOH (50 mL) and stirred at RT overnight. The solution was concentrated. The product was purified from the crude concentrate via silica gel column chromatography (RediSep 40 g column) using 0-100% 90/10/1 (DCM/MeOH/ammonia) in DCM to afford 7′-bromo-4′-fluoro-2′-methoxy-3,4-dihydro-2H-spiro[imidazo[1,5-a]pyrimidine-8,9′-xanthen]-6-amine (150 mg, 0.348 mmol). MS m/z=431.0 [M+H].

Workup

  1. concentrationThe solution was concentrated
  2. customThe product was purified from the crude
  3. concentrationconcentrate via silica gel column chromatography (RediSep 40 g column)

Sources & evidence

ORD record
ord-0d2cd996c7414f609c48b3fed9e55786
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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