Dimethylamine → 3-[4-(Dimethylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile

HRID 1750275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750275
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:19][NH:20][CH3:21].C(N(CC)CC)C>C(O)CCC>[CH3:19][N:20]([CH3:21])[C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 867069533-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile

Produkt 1

HCID 727068413-[4-(Dimethylamino)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile (C14) (157 mg, 0.616 mmol), dimethylamine (189 mg, 4.19 mmol) and triethylamine (182 mg, 1.80 mmol) in n-butanol (12 mL) was heated under microwave irradiation at 150° C. for 25 minutes. After concentration in vacuo, the residue was purified by preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 25% to 65% B) to give the product as a white solid. Yield: 72.1 mg, 0.274 mmol, 44%. LCMS m/z 263.8 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 12.15 (br s, 1H), 8.28 (s, 1H), 7.93 (br s, 1H), 7.78 (br d, J=7.8 Hz, 1H), 7.73 (br d, J=7.8 Hz, 1H), 7.62 (br dd, J=8.0, 7.8 Hz, 1H), 7.57 (br s, 1H), 2.73 (s, 6H).

Aufarbeitung

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified by preparative HPLC (Column: Phenomenex Gemini C18, 8 μm; Mobile phase A: ammonia in water, pH 10; Mobile phase B: acetonitrile; Gradient: 25% to 65% B)

Quellen und Nachweise

ORD-Eintrag
ord-e0b0d6d48e64499cbabbbb5c55473eb4
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156845B2

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