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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → 1,1-Dimethylethyl 3',6'-dihydro-5-(2-pyrimidinyl)[2,4'-bipyridine]-1'(2'h)-carboxylate

HRID 1038091
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HRID 1038091 반응식
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH:25]=[C:24](B(O)O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH:23]=[C:24]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[CH:6][N:7]=2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 21931462(1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acidHCID 534869812-(6-Bromopyridin-3-yl)pyrimidine

생성물 1

HCID 589464631,1-Dimethylethyl 3',6'-dihydro-5-(2-pyrimidinyl)[2,4'-bipyridine]-1'(2'h)-carboxylate

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

Refluxed mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine (1Q) (200 mg, 0.85 mmol), N-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (290 mg, 0.93 mmol); Cesium Carbonate (500 mg, 1.538 mmol); PdCl2dppf (30 mg) in dioxane/H2O (10 ml v/v 4/1) for 4 hours. Cooled reaction, then evaporated solvent. Extracted with EtOAc (200 ml) washed with H2O (50 ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110 mg, 38%) ESMS (MH, 339).

후처리

  1. temperatureRefluxed
  2. temperatureCooled
  3. customreaction
  4. extractionExtracted with EtOAc (200 ml)
  5. washwashed with H2O (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvent evaporated
  9. customyielding a solid which
  10. customchromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110 mg, 38%) ESMS (MH, 339)

출처 및 근거

ORD 기록
ord-0182a585d8d14053b52688b8c9c07cfa
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546404B2

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