(Diethylamino)sulfur trifluoride → (4-Fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl ester

HRID 626693ノート

反応式

HRID 626693 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[N:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[N:13]=[C:12]([CH2:14][F:23])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 83854419tert-butyl N-[4-(hydroxymethyl)pyrimidin-2-yl]carbamate

生成物 1

HCID 69674809(4-Fluoromethylpyrimidin-2-yl)carbamic acid tert-butyl ester収率 32%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (4-hydroxymethylpyrimidin-2-yl)carbamic acid tert-butyl ester (450 mg, 2.0 mmol) in DCM (10 mL) at 0° C. was treated with DAST (396 μL, 3.0 mmol) and stirred for 10 minutes. The reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (50% ethyl acetate in cyclohexane) to afford the title compound as a white solid (144 mg, 32% yield). 1H NMR (300 MHz, CDCl3): δ 8.64 (d, J=5.1 Hz, 1H), 7.53 (s, 1H), 7.15-7.12 (m, 1H), 5.45-5.44 (m, 1H), 5.33-5.32 (m, 1H), 1.54 (s, 9H).

後処理

  1. customThe reaction mixture was partitioned between DCM and sodium bicarbonate (sat. aq.)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (50% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-ff0e90e5cb284b07a37a9e21ca5554f3
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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