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Sodium Carbonate → (S)-1-methyl-3-(4-(4-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea

HRID 1771551
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HRID 1771551 반응식
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[CH:4][N:3]=1.[CH2:15]([NH:17][C:18](=[O:35])[NH:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=1)C.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCO.O>[CH3:15][NH:17][C:18]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[CH:5]=[CH:4][N:3]=2)=[CH:22][CH:21]=1)=[O:35]
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 44119377N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 72942067(S)-4-(2-Chloropyrimidin-4-yl)-3-methylmorpholine2회

생성물 1

HCID 53380856(S)-1-methyl-3-(4-(4-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea수율 8%

시약·촉매·용매 1

HCID 86587095
Dimethoxyethane ethanol water
용매

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온도
120 °C

실험 절차

To a solution of (S)-4-(2-chloropyrimidin-4-yl)-3-methylmorpholine (Intermediate 3) (100 mg, 0.47 mmol) and 4-(3-ethylureido)phenylboronic acid pinacol ester (143 mg, 0.52 mmol) in DME:EtOH:H2O (12:5:3, 2 mL) was added Pd(PPh3)2(Cl)2 (17 mg, 0.024 mmol) and Na2CO3 (149 mg, 1.41 mmol). The reaction mixture was then heated by microwave at 120° C. for 1 h. The crude reaction mixture was then partitioned between water and EtOAc, the phases separated and the organic layer washed with aqueous NaHCO3 and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (2-5% MeOH/DCM) to yield a white solid (12 mg, 8%).

후처리

  1. customThe crude reaction mixture
  2. customwas then partitioned between water and EtOAc
  3. customthe phases separated
  4. washthe organic layer washed with aqueous NaHCO3 and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by flash chromatography (2-5% MeOH/DCM)

출처 및 근거

ORD 기록
ord-85683600bd364f7bab535de1b09c21c5
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249129B2

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