Potassium Carbonate → (S)-1-(5-bromopyrimidin-2-yl)ethanol

HRID 1399984노트

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HRID 1399984 반응식
[Br:1]/[C:2](=[CH:5]\N(C)C)/[CH:3]=O.C(=O)([O-])[O-].[K+].[K+].Cl.[OH:16][C:17]([CH3:22])(C)[C:18]([NH2:20])=[NH:19]>C(O)C>[Br:1][C:2]1[CH:3]=[N:19][C:18]([C@@H:17]([OH:16])[CH3:22])=[N:20][CH:5]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 215914792-Bromo-3-(dimethylamino)acroleinHCID 426142842-Hydroxy-2-methylpropanimidamide hydrochloride

생성물 1

HCID 86696897(S)-1-(5-bromopyrimidin-2-yl)ethanol수율 16%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
85 °C

실험 절차

(Z)-2-bromo-3-(dimethylamino)prop-2-enal (11.5 g), potassium carbonate (13.4 g), ethanol (200 mL) and 2-hydroxy-2-methyl-propanamidine hydrochloride (12.1 g) were placed in a flask and the mixture heated at 85° C. overnight. The reaction mixture was cooled and the mixture filtered, washed with ethanol and the combined filtrates concentrated in vacuo with silica gel. This residue was purified by chromatography on silica, eluting with 0-50% ethyl acetate in heptane to give (1S)-1-(5-bromopyrimidin-2-yl)ethanol as a white solid (2.1 g, 16%). 1H NMR (CDCl3) δ 8.83 (s, 2H), 4.98 (m, 1H), 3.8 (m, 1H), 1.6 (d, J=6.6 Hz, 3H). Chiral HPLC: Column. Chirapak IC, 0.46 cm×25 cm; 20 min isocratic gradent; 5:95 EtOH:n-hexane+0.1% diethylamine) retention time=14.08 min. (racemic mixture: ˜14.5 min: S isomer; ˜17.5 min: R isomer).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe mixture filtered
  3. washwashed with ethanol
  4. concentrationthe combined filtrates concentrated in vacuo with silica gel
  5. customThis residue was purified by chromatography on silica
  6. washeluting with 0-50% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-eedb5706b2a841bf8e35ee149a0c0812
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906902B2

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