Sodium Bicarbonate → N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine

HRID 911151Notes

Reaction equation

HRID 911151 reaction equation
Cl.CS[C:4]1[N:9]=[C:8]([C:10]2[C:11]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:27]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[N:26][N:25]=4)=[CH:19][CH:18]=3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][N:5]=1.O[O:41][S:42]([O-:44])=O.[K+].[C:46]([O-])(O)=O.[Na+]>CO>[CH3:46][S:42]([C:4]1[N:9]=[C:8]([C:10]2[C:11]([O:16][C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24]4[C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[C:27]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[N:26][N:25]=4)=[CH:21][CH:22]=3)=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][N:5]=1)(=[O:44])=[O:41]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 66731379N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine hydrochloride

Product 1

HCID 66731697N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 ml dried round bottom flask was charged with N-(4-(3-(2-(methylthio)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine hydrochloride (1.25 g, 2.27 mmol) and sonicated in methanol (20.6 ml, 0.11 M) for 20 minutes. To this was added oxone (4.18 g, 6.81 mmol) and the mixture was stirred at RT for 2 days. The mixture was cooled to 0° C. and basified with aq. NaHCO3. The solids were filtered, washed with water, and dried under high vacuum to provide N-(4-(3-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)-4-phenylphthalazin-1-amine as a light yellow solid. MS m/z=547 [M+H]+. Calc'd for C30H22N6O3S: 546.60.

Workup

  1. customA 100 ml dried round bottom flask
  2. filtrationThe solids were filtered
  3. washwashed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-19197313170a4f968e18534dac7e7807
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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