Iodoethane → 5-[5-(Ethylsulfonyl)-4-methoxy-2-(1-methylethyl)phenoxy]-2,4-pyrimidinediamine

HRID 1677309Notes

Reaction equation

S([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[N:13]=[C:12]([NH2:14])[C:11]([O:15][C:16]2[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:18][C:19]([O:26][CH3:27])=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:21]=2)=[CH:10][N:9]=1.C(=O)(O)[O-].[Na+].[CH2:36](I)[CH3:37]>O.O1CCOCC1>[CH2:36]([S:22]([C:20]1[C:19]([O:26][CH3:27])=[CH:18][C:17]([CH:28]([CH3:30])[CH3:29])=[C:16]([CH:21]=1)[O:15][C:11]1[C:12]([NH2:14])=[N:13][C:8]([NH2:7])=[N:9][CH:10]=1)(=[O:24])=[O:23])[CH3:37]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of sodium sulfite (541 mg, 4.29 mmol) in water (20 mL) was added 5-(2,4-Diamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzenesulfonyl chloride (400 mg, 1.07 mmol) and the reaction was heated at 80° C. for 1 hour. Sodium bicarbonate (361 mg, 4.29 mmol-dissolved in 5 mL water), dioxane (20 mL), and ethyl iodide (0.10 mL, 1.29 mmol) were added and the reaction was heated at 80° C. for 2 hours. The reaction was concentrated, extracted with dichloromethane (150 mL) and water (20 mL). The dichloromethane layer was dried using anhydrous sodium sulfate, concentrated, and purified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide) to yield 5-(5-ethanesulfonyl-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (77 mg, 20%) as white solid, MS (M+H)=367.

Workup

temperaturethe reaction was heated at 80° C. for 2 hours
concentrationThe reaction was concentrated
extractionextracted with dichloromethane (150 mL) and water (20 mL)
dry with materialThe dichloromethane layer was dried
concentrationconcentrated
custompurified via silica gel column chromatography (95/5/0.1 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record: ord-9ebbc973ad0745fdb668301c2d1f77d1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008313B2

Reaction notes

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