반응 #86427

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

TFA

DCM

→

title compound

수율 58.0%

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

수율 58.0%

반응 조건

후처리

1. 1
   기타The solution was evaporated to dryness
2. 2
   workup.ADDITIONdiluted with DCM (40 mL)
3. 3
   세척washed with 10% saturated Na2CO3 (10 mL)
4. 4
   건조The DCM layer was dried over anhydrous Na2SO4
5. 5
   농축Concentration under vacuum
6. 6
   기타gave crude product, which
7. 7
   기타was purified by silica gel column chromatography (10% MeOH/DCM with 0.5% Et3N)

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-3-(2-trimethylsilanyl-ethoxymethyl)-urea in anhydrous DCM (10 mL) was added TFA (10 mL) at room temperature. The solution was stirred at room temperature for 3 hours. LCMS showed major product peak. The solution was evaporated to dryness, diluted with DCM (40 mL) and washed with 10% saturated Na2CO3 (10 mL). The DCM layer was dried over anhydrous Na2SO4. Concentration under vacuum gave crude product, which was purified by silica gel column chromatography (10% MeOH/DCM with 0.5% Et3N) to afford the title compound (45 mg, yield: 58% in two steps). MS (ESI): 520 [M+H]+.

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