Tetrahydrofuran → 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylsulfinyl)ethyl]benzamide

HRID 1864072Notes

Reaction equation

HRID 1864072 reaction equation
[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:36]=[CH:35][CH:34]=[CH:33][C:25]=2[C:26]([NH:28][CH2:29][CH2:30][S:31][CH3:32])=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:10]=2)=[N:6][CH:7]=1.[OH:37][O:38][S:39]([O-:41])=O.[K+].[CH2:43]1COCC1>CO.O>[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:36]=[CH:35][CH:34]=[CH:33][C:25]=2[C:26]([NH:28][CH2:29][CH2:30][S:31]([CH3:32])=[O:37])=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:10]=2)=[N:6][CH:7]=1.[F:1][C:2]1[C:3]([NH:23][C:24]2[CH:36]=[CH:35][CH:34]=[CH:33][C:25]=2[C:26]([NH:28][CH2:29][CH2:30][S:39]([CH3:43])(=[O:41])=[O:38])=[O:27])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 579741382-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylthio)ethyl]benzamide

Product 2

HCID 579741982-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylsulfinyl)ethyl]benzamideHCID 579742062-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylsulfonyl)ethyl]benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylthio)ethyl]benzamide (100 mg, 0.20 mmoles) was dissolved in 5 mL of THF and 5 mL of methanol, and treated with a solution of OXONE® reagent (a registered trademark of DuPont, 15 equivalents) in 5 mL water. The system was stirred for 48 h at room temperature, and then filtered and concentrated to dryness. The residue was immobilized onto silica gel and purified by silica gel chromatography, using a gradient of 100% A to 90% A-10% B, where “A” is chloroform and “B” is 10:90:1 methanol-chloroform-concentrated aqueous ammonium hydroxide). The title compounds 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylsulfinyl)ethyl]benzamide (Example 187) and 2-{[5-fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-[2-(methylsulfonyl)ethyl]benzamide were isolated and characterized.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-a5f326725ea54de5b445d8433d0a8efe
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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