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

HRID 1399984ノート

反応式

HRID 1399984 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
85 °C

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-eedb5706b2a841bf8e35ee149a0c0812
出典データセット
uspto-grants-2014_12
特許番号
US08906902B2

反応ノート

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