Sodium Carbonate → 5-(3-Chloropyridin-4-yl)-N4-cyclopentylpyrimidine-2,4-diamine

HRID 875937

반응식

HRID 875937 반응식
Br[C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:21]=1[C:2]1[C:3]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 38618773-Chloro-4-pyridineboronic acidHCID 582998155-Bromo-N4-cyclopentylpyrimidine-2,4-diamine

생성물 1

HCID 582995755-(3-Chloropyridin-4-yl)-N4-cyclopentylpyrimidine-2,4-diamine수율 80%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

To a solution of 2 (2.57 g, 10.0 mmol) in dioxane (75 mL) were added 3-chloropyridine-4-boronic acid (4.72 g, 10.0 mmol), trans-dichlorobis(triphenylphosphine)-palladium(II) (702 mg, 1.0 mmol), and sodium carbonate (3.82 g, 36 mmol, in 36 mL of water). The mixture thus obtained was purged with N2 for 10 min and heated at 120° C. in a sealed tube for 22 h. The reaction mixture was diluted with water and the product was extracted with chloroform. The organic layers were dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane to give the title compound (3) as a white solid (2.31 g, 80%). 1H NMR (500 MHz, DMSO-d6) δ 8.64 (1H, s), 8.50 (1H, d, J=4.9 Hz), 7.51 (1H, s), 7.34 (1H, d, 1H, J=4.9 Hz), 6.21 (2H, d, 1H, br s), 5.97 (1H, d, J=7.6 Hz), 4.43 (1H, p, J=7.4 Hz), 1.84 (2H, m), 1.62 (2H, m), 1.40-1.49 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 290.0, Calculated 290.1.

후처리

  1. customThe mixture thus obtained
  2. customwas purged with N2 for 10 min
  3. additionThe reaction mixture was diluted with water
  4. extractionthe product was extracted with chloroform
  5. dry with materialThe organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 2.5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-c030b3f3827e45b0b8487476b3a178c5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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