Triethylamine → HCID 178461601, 화합물

HRID 522809노트

반응식

HRID 522809 반응식
Br[C:2]1[NH:3][C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][C@H:12]1[CH3:17])[N:7]=[C:6]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][C@@H:19]1[CH3:24])[N:5]=2.[NH:25]1[CH:29]=[CH:28][C:27](B(O)O)=[N:26]1.CCN(CC)CC>C(COC)OC.O.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:24][C@H:19]1[CH2:20][O:21][CH2:22][CH2:23][N:18]1[C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([C:29]3[CH:28]=[CH:27][NH:26][N:25]=3)[NH:3]2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:7]=1

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 178461599HCID 178461599, 화합물HCID 178514837HCID 178514837, 화합물

생성물 1

HCID 178461601HCID 178461601, 화합물수율 39.2%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

8-Bromo-2-((S)-3-methyl-morpholin-4-yl)-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (50 mg, 126 μmol) was dissolved in dimethoxyethane (2 mL) and water (0.2 mL), followed by addition of 1H-pyrazole-3-ylboronic acid (21.1 mg, 189 μmol), PdCl2(dppf) (9.21 mg, 13 μmol) and NEt3 (53 μl, 378 μmol) under argon. The reaction mixture was heated to 85° C. for 23 hours. The reaction mixture was then diluted with EtOAc, the organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (12 g SiO2, EtOAc) to give the product (19 mg, 39% yield).

후처리

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (12 g SiO2, EtOAc)

출처 및 근거

ORD 기록
ord-8445d1de8ad647769629ef46a8d250aa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334271B2

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