Sodium Carbonate → 2-(4-Fluorophenyl)-1-(2-(1-(S)-phenylethyl)amino-4-primidinyl)-5-aminoimidazo[4,5-b]pyridine

HRID 396376

Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](SC)[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.C([O-])([O-])=O.[Na+].[Na+].[C:43]1([C@@H:49]([NH2:51])[CH3:50])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:51][C@H:49]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH3:50])[N:19]=3)[C:10]3[C:11]([N:17]=2)=[N:12][C:13]([NH2:16])=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

2-(4-Fluorophenyl)-1-(2-methylthio-4-pyrimidinyl)-5-aminoimidazo[4,5-b]pyridine (110 mg, 0.31 mmol) is dissolved in CH2Cl2/HOAc 1:1 (6.2 ml), combined at 0° C. with mCPBA (84 mg 70% 0.34 mmol) and stirred for 30 min. The reaction mixture is poured on 2N Na2CO3 and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to yield the crude sulfoxide (110 mg). 50 mg are dissolved in 1-(S)-phenylethylamine (0.5 ml) and heated to 120° C. for 1 h. Purification over RP18 (CH3CN/Water 70/30 to 10/90) yielded the title compound as light brown foam (30 mg 52%)

Aufarbeitung

extractionextracted with ethyl acetate three times
dry with materialThe combined organic phases are dried over Na2SO4
filtrationfiltered
customevaporated to dryness
customto yield the crude sulfoxide (110 mg)
customPurification over RP18 (CH3CN/Water 70/30 to 10/90)

Quellen und Nachweise

ORD-Eintrag: ord-e0517b94d44b489cb932683350041fdf
Quelldatensatz: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06608072B1

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