Tetrahydrofuran → 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

HRID 502785

Reaktionsgleichung

Reaktionsgleichung von HRID 502785
[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.C1COCC1.[CH2:19]([N:21](CC)CC)C.Cl.CN>O>[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5]([NH:21][CH3:19])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 574288715-Bromo-2-chloro-4-(thiophen-2-yl)pyrimidine

Produkt 1

HCID 684594085-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A 16 by 100 mm vial was charged with 5-bromo-2-chloro-4-(thiophen-2-yl)pyrimidine (1.00 g, 3.6 mmol), THF (4 mL), triethylamine (1.5 ml, 11 mmol), and methylamine hydrochloride (0.49 g, 7.3 mmol), and water (0.4 mL). The vial was capped and heated to 85° C. with stirring for 20 hours. The reaction was cooled to room temperature and concentrated. The residue was purified via column chromatography on silica gel (gradient elution with 0 to 4% methanol in dichloromethane) to afford 5-bromo-N-methyl-4-(thiophen-2-yl)pyrimidin-2-amine. MS m/z=271 [M+H]+. Calc'd for C9H8BrN3S: 270.

Aufarbeitung

  1. customThe vial was capped
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified via column chromatography on silica gel (gradient elution with 0 to 4% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a2f2312c23c944e89b950f79692acdec
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776869B2

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