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alpha-Chlorohydrin, (+)- → 3-{2-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diol

HRID 2069474
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HRID 2069474 반응식
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][CH:22]([CH3:24])[CH3:23])[N:15]=3)=[CH:12][N:13]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].Cl[CH2:28][C@@H:29]([OH:32])[CH2:30][OH:31]>CC(O)C.[OH-].[Na+].CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][CH:22]([CH3:23])[CH3:24])[N:15]=3)=[CH:12][N:13]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[O:26][CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[CH3:2]
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HCID 148904alpha-Chlorohydrin, (+)-HCID 1363463712-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol

생성물 1

HCID 685050023-{2-Ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diol수율 24.8%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8857
Ethyl Acetate
용매
HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenol (30 mg, 85 μmol) in iPrOH (4 mL), 3M aq. NaOH (1 mL) followed by (S)-3-chloro-propane-1,2-diol (67 μL, 0.85 mmol) is added. The reaction mixture is stirred at rt for 15 h, and is then diluted with EtOAc and washed with 1M aq. NaOH followed by brine. The org. solution is dried over Na2SO4, filtered and evaporated to give 3-{2-ethyl-4-[5-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-oxazol-2-yl]-6-methyl-phenoxy}-propane-1,2-diol (9 mg) as a yellow solid; LC-MS: tR=0.79 min, [M+H]+=426.80.

후처리

  1. additionis added
  2. washwashed with 1M aq. NaOH
  3. dry with materialsolution is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-64cd5bf1a110476799ce809c236d163a
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08299086B2

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