반응 #86428

반응 방정식

1-[6-(2-amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-urea

acryloyl chloride

→

title compound

수율 15.0%

N-(2-{6-[3-(2,6-Dichloro-3,5-dimethoxy-phenyl)-1-methyl-ureido]-pyrimidin-4-ylamino}-5-dimethylaminomethyl-phenyl)-acrylamide

수율 15.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타The reaction was quenched with MeOH (3 mL)
2. 2
   기타evaporated
3. 3
   기타The residue was purified by prep-HPLC (water/ACN in NH4HCO3 condition)

실험 절차

To a stirred solution of 1-[6-(2-amino-4-dimethylaminomethyl-phenylamino)-pyrimidin-4-yl]-3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-urea (45 g, 0.11 mmol) in THF (40 mL) at −10° C. was added acryloyl chloride (30 g, 0.33 mmol) in THF (3 mL). The solution was stirred at −10° C. for 5 hours. LCMS showed major product peak. The reaction was quenched with MeOH (3 mL) and evaporated. The residue was purified by prep-HPLC (water/ACN in NH4HCO3 condition) to afford the title compound (6 mg, yield: 15%). 1H-NMR (400 MHz, MeOH-d4) δ 8.25 (s, 1H), 7.47 (d, 1H), 7.44 (s, 1H), 7.16 (dd, 1H), 6.70 (s, 1H), 6.33-6.20 (m, 3H), 5.67 (dd, 1H), 3.84 (s, 6H), 3.43 (s, 2H) 3.22 (s, 3H), 2.20 (s, 6H); MS (ESI): 574 [M+H]+.

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