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Sodium Carbonate → (3R,4S)-1-Pyridin-3-yl-4-(4-pyrimidin-5-yl-phenoxy)pentan-3-ol

HRID 1856706
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HRID 1856706 반응식
[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:25]=[N:26][CH:27]=[N:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][CH2:15][C@@H:2]([OH:1])[C@@H:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([C:24]3[CH:25]=[N:26][CH:27]=[N:28][CH:29]=3)=[CH:7][CH:6]=2)[CH3:14])[CH:18]=1
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 54413593(1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid

생성물 1

HCID 53887381(3R,4S)-1-Pyridin-3-yl-4-(4-pyrimidin-5-yl-phenoxy)pentan-3-ol수율 31.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

Prepared according to the method described in Example 21b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.200 g, Example 21a)), 5-bromopyrimidine (0.159 g), ethanol (3 ml), 2M aqueous sodium carbonate (0.67 ml) and tetrakistriphenylphosphine palladium(0) (0.030 g) with heating at 90° C. for 4 hours. After work up, the residue was purified by reverse phase HPLC, eluting with a gradient of 15:85 to 95:5 acetonitrile in 0.1M ammonium acetate. The compound was subsequently purified by flash chromatography on silica gel, eluting with 1:1 isohexane/acetone to give the title compound as an oil (0.070 g).

후처리

  1. customPrepared
  2. customAfter work up, the residue was purified by reverse phase HPLC
  3. washeluting with a gradient of 15:85 to 95:5 acetonitrile in 0.1M ammonium acetate
  4. customThe compound was subsequently purified by flash chromatography on silica gel
  5. washeluting with 1:1 isohexane/acetone

출처 및 근거

ORD 기록
ord-6fbb52769fbb4deaa6c5198bf9ee7b42
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06143751

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