2-(Dimethylamino)ethanol → [2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine

HRID 1910032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910032
[Br:1][C:2]1[C:10]2[C:5]([NH:6][CH:7]=[N:8][C:9]=2[Cl:11])=[N:4][CH:3]=1.[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:15][CH2:14][N:13]([CH3:17])[CH3:12])[CH:3]=1

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178478408HCID 178478408, Verbindung

Produkt 1

HCID 86663684[2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-4-chloro-1H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.860 mmol), 2-(dimethylamino)ethanol (230 mg, 2.58 mmol) and triphenylphosphine (451 mg, 1.721 mmol) in Tetrahydrofuran (THF) (10 mL) was added dropwise DEAD (0.272 mL, 1.721 mmol). The solution was allowed to stir at room temperature. After 2 hr the reaction was concentrated then loaded on to a 25 g Biotage SNAP column and eluted with 0 to 8% MeOH in DCM gradient over 30 minutes to give [2-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl]dimethylamine (175 mg, 67.0% yield) as a white solid. LC/MS (ES) m/z=303.1, 305.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.04 (s, 1H), 4.36 (t, J=6.19 Hz, 2H), 2.67 (t, J=6.19 Hz, 2H), 2.16 (s, 6H).

Aufarbeitung

  1. concentrationAfter 2 hr the reaction was concentrated
  2. washeluted with 0 to 8% MeOH in DCM gradient over 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-6e57f09361bb455ea3bd19cabbcfe0c0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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