Reaktion #6957

Reaktionsgleichung

5-[2-(3-aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

N,N-diethyl-2-aminobromoethane

HBr

sodium t-butoxide

→

4-Cyclohexyl-5-{2-[3-(2-diethylamino-ethylamino)-phenylamino]-5-methyl-pyrimidin-4-yl}2-methylsulfanyl-thiophene-3-carbonitrile

Ausbeute 33.0%

Lösungsmittel

CH2Cl2

MeOH

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was partitioned between EtOAc and water
2. 2
   Trocknenthe organics were dried over sodium sulfate
3. 3
   Einengenthen concentrated in vacuo
4. 4
   SonstigeThe crude product was purified by chromatography (silica gel, 5% MeOH:CH2Cl2)
5. 5
   Sonstigeto afford VI-26 in 33% yield

Vorschrift

To a solution of 5-[2-(3-aminophenylamino)-5-methyl-pyrimidin-4-yl]-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile (20 mg, 45.91 micromol) and N,N-diethyl-2-aminobromoethane.HBr (12 mg, 45.91 micromol) in THF was added sodium t-butoxide (9 mg, 91.82 micromol) and the reaction was stirred at ambient temperature overnight. TLC indicated conversion to product (10% MeOH:CH2Cl2). The reaction was partitioned between EtOAc and water, the organics were dried over sodium sulfate then concentrated in vacuo. The crude product was purified by chromatography (silica gel, 5% MeOH:CH2Cl2) to afford VI-26 in 33% yield. δ 0.95 (bs, 6H), 1.0–1.8 (m, 10H), 2.0 (s, 3H), 2.6 (s, 3H), 2.75 (bs, 2H), 3.4 (s, 1H), 3.6 (bs, 2H), 4.0 (bs, 2H), 5.2 (s, 1H), 6.5 (d, 1H), 6.55 (s, 1H), 6.6 (d, 1H), 7.0 (t, 1H), 8.1 (s, 1H).

Quelle