(2,6-Dimethoxypyridin-3-yl)boronic acid → N4-Cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine

HRID 875990노트

반응식

HRID 875990 반응식
CC(C)(C[N:6]1[C:10]2[N:11]=[C:12]([NH:15]C3C=CC(N4CCNCC4)=CN=3)[N:13]=[CH:14][C:9]=2[C:8]2[CH:28]=[CH:29]N=[CH:31][C:7]1=2)CO.[CH3:33][O:34][C:35]1[C:40](B(O)O)=[CH:39][CH:38]=[C:37]([O:44][CH3:45])[N:36]=1.C1(P(C2CCCCC2)C2C(OC)=CC=CC=2OC)CCCCC1>C(O)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:7]1([NH:6][C:10]2[C:9]([C:40]3[C:35]([O:34][CH3:33])=[N:36][C:37]([O:44][CH3:45])=[CH:38][CH:39]=3)=[CH:14][N:13]=[C:12]([NH2:15])[N:11]=2)[CH2:8][CH2:28][CH2:29][CH2:31]1

참가 물질

6

반응물 3

HCID 2762707(2,6-Dimethoxypyridin-3-yl)boronic acidHCID 57474835Dicyclohexyl(2,6-dimethoxyphenyl)phosphineHCID 582997172,2-Dimethyl-3-[2-(5-piperazin-1-yl-pyridin-2-ylamino)-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-9-yl]-propan-1-ol

생성물 1

HCID 67234124N4-Cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine수율 53%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 2631-Butanol용매

반응 조건

온도
100 °C

실험 절차

Compound 2 (2.00 g, 7.78 mmol), 2,6-dimethoxypyridin-3-ylboronic acid (2.13 g, 11.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.214 g, 0.233 mmol), and dicyclohexyl(2,6-dimethoxyphenyl)phosphine (0.156 g, 0.467 mmol), were dissolved in n-butanol (2.5 mL). The reaction was purged with argon and heated at 100° C. for 19 hours. The resulting solution was added to 80 mL water and extracted with ethyl acetate (2×150 mL). The combined organics were dried (MgSO4) and evaporated to give an orange oil. Silica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-5% methanol) afforded compound 267 as an off-white solid (1.29 g, 53%).

후처리

  1. customThe reaction was purged with argon
  2. additionThe resulting solution was added to 80 mL water
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. customevaporated
  6. customto give an orange oil
  7. washSilica gel chromatography (gradient elution dichloromethane+2.5% TEA/0-5% methanol)

출처 및 근거

ORD 기록
ord-18dceb8bae5f4ddda46770443bfbfaff
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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