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

HRID 626693노트

반응식

HRID 626693 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff0e90e5cb284b07a37a9e21ca5554f3
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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