m-Chloroperbenzoic acid → 1-(4'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-ylamino)-2-methylpropan-2-ol

HRID 1397146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397146
[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:8]=[C:7]([NH:19][CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])[N:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>C(Cl)Cl>[CH:1]1([CH2:4][C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17]([CH3:18])=[O:33])[N:12]=3)=[CH:9][N:8]=[C:7]([NH:19][CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])[N:6]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 679836451-(4'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-ylamino)-2-methylpropan-2-ol

Produkt 1

HCID 679836401-(4'-(Cyclopropylmethyl)-2-(methylsulfinyl)-4,5'-bipyrimidin-2'-ylamino)-2-methylpropan-2-olAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4′-(Cyclopropylmethyl)-2-(methylthio)-4,5′-bipyrimidin-2′-ylamino)-2-methylpropan-2-ol (90 mg, 0.261 mmol) in DCM (521 μl), mCPBA (70.6 mg, 0.287 mmol) was added in portions, and the reaction mixture was stirred at rt for 1 h. The crude product was purified by a Biotage silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product as a yellow solid (38 mg, 40% yield). MS (ES+): m/z=362.2 (100) [MH+]. HPLC: tR=0.90 min over 3 min. Purity: 100% [HPLC (LC/MS) at 220 nm].

Aufarbeitung

  1. customThe crude product was purified by a Biotage silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM]

Quellen und Nachweise

ORD-Eintrag
ord-9cfe45a468114f7d8ee9cdc42336fda9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901147B2

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