Hydrochloric Acid → 2-phenyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4(3H)-one

HRID 68336Notes

Reaction equation

HRID 68336 reaction equation
C[O:2][C:3]1[N:8]=[C:7](S(C)(=O)=O)[N:6]=[C:5]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15](S(C3C=CC=CC=3)(=O)=O)[CH:14]=2)[CH:4]=1.[C:31]1([Mg]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)C.[OH-].[Na+].Cl>COCCOC>[C:31]1([C:7]2[NH:8][C:3](=[O:2])[CH:4]=[C:5]([C:13]3[C:21]4[C:16](=[N:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)[N:6]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 668887123-(6-methoxy-2-(methylsulfonyl)pyrimidin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418255HCID 178418255, compound

Product 1

HCID 1359628572-phenyl-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of EXAMPLE 1B (89 mg, 0.20 mmol) in 1,2-dimethoxyethane (2 mL) at 0° C. was added dropwise 3M phenylmagnesium bromide in diethyl ether (0.133 mL, 0.40 mmol)). The mixture was slowly warmed to room temperature and stirred for 15 minutes. To the solution was added dropwise 1M aqueous sodium hydroxide (2 mL, 2 mmol). The mixture was stirred at room temperature for 1 day and concentrated. The residue was dissolved in 12% aqueous HCl (0.62 mL, 2.25 mmol) and heated at 90° C. for 4 hours. The mixture was concentrated and purified by reverse phase HPLC to provide the title compound. MS (ESI) m/e 289 (M+H)+; 1H NMR (DMSO-d6) δ 6.78 (s, 1H), 7.25 (dd, J=7.93, 4.58 Hz, 1H), 7.54-7.65 (m, 3H), 8.24-8.34 (m, 3H), 8.44 (s, 1H), 8.69-8.75 (m, 1H), 12.32 (s, 1H).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 day
  2. concentrationconcentrated
  3. temperatureheated at 90° C. for 4 hours
  4. concentrationThe mixture was concentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-91eabbb6b2844ddcac824f6090c21573
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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