Reaktion #360141

Reaktionsgleichung

{4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine

2-chloropyrimidine

N,N-diisopropylethylamine

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title compound

Ausbeute 17.7%

N-{[4-(4-(3-Pyrrolidin-1-ylpropoxy)phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyrimidin-2-amine

Ausbeute 17.7%

Lösungsmittel

N-methylpyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between ethyl acetate (10 ml) and saturated NaHCO3 (10 ml)
2. 2
   TrocknenThe organic washings were dried over Na2SO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigeto give an oil
5. 5
   SonstigeThe compound was purified by column chromatography on silica gel
6. 6
   Wascheneluting with dichloromethane
7. 7
   SonstigeCompound still impure so purified further on the Fraction Lynx automated LC system

Vorschrift

A mixture of {4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-yl}methylamine (100 mg, 0.314 mmol), 2-chloropyrimidine (50 mg, 0.346 mmol) and N,N-diisopropylethylamine (112 μl, 0.629 mmol) in N-methylpyrrolidinone (0.5 ml) was heated at 180° C. in the microwave (Smith Personal Synthesiser) for 600 seconds. The reaction mixture was partitioned between ethyl acetate (10 ml) and saturated NaHCO3 (10 ml). The organic washings were dried over Na2SO4 and concentrated in vacuo to give an oil. The compound was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:ammonia, 100:0:0 to 88:12:1.2. Compound still impure so purified further on the Fraction Lynx automated LC system to give the title compound as a solid (22 mg, 17%) 1H NMR (400 MHz, CDCl3) δ 8.30 (brs, 2H), 7.34 (d, 2H), 6.92 (d, 2H), 6.70 (t, 1H), 4.10 (t, 2H), 3.78-3.84 (m, 2H), 3.62-3.72 (multiple peaks, 4H), 3.44-3.55 (m, 2H), 3.40 (m, 2H), 3.04-3.18 (m, 2H), 1.85-2.25 (multiple peaks, 10H).

Quelle