반응 #565373

반응 방정식

3-Nitrophenylguanidine

4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile

DMF-DMA

→

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

수율 42.0%

용매

—

hexanes

—

hexanes

EtOAc

DMF

EtOAc

toluene

반응 조건

후처리

1. 1
   기타resulting in conversion to product
2. 2
   온도heated at 120° C. overnight
3. 3
   기타resulting in conversion to product
4. 4
   기타The reaction was partitioned between EtOAc and water
5. 5
   건조the organics were dried over sodium sulfate
6. 6
   농축then concentrated in vacuo
7. 7
   기타The crude product was purified by chromatography (silica gel, 10% EtOAC:hexanes)
8. 8
   기타to afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps

실험 절차

To a solution of 4-cyclohexyl-5-(3-dimethylamino-2-methyl-acryloyl)-2-methylsulfanyl-thiophene-3-carbonitrile (0.5 g, 1.7 mmol) in toluene (3 ml) was added DMF-DMA and the reaction was heated at 90° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). The crude product was combined with DMF (10 ml) and 3-Nitrophenylguanidine (0.5 g, 2.78 mmol) in a sealed tube and heated at 120° C. overnight resulting in conversion to product as determined by TLC (40% EtOAc:hexanes). 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, 10% EtOAC:hexanes) to afford 0.334 g (3.05 umol) of V-7 in 42% yield for 2 steps. 1H NMR (CDCl3) δ1.0-2.0 (m, 10H), 2.1 (s, 3H), 2.6(s, 3H), 7.4(m, 1H), 7.7 (d, 1H), 7.8 (d, 1H), 8.3 (s, 1H), 8.7 (s, 1H).

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