Sodium Cyanide → 4-Cyclopropylpyrimidine-2-carbonitrile

HRID 931126노트

반응식

HRID 931126 반응식
[N:1]1(C2CCCCCCC2)[CH2:8]CCCCCN1.Cl[C:18]1[N:23]=[C:22]([CH:24]2[CH2:26][CH2:25]2)[CH:21]=[CH:20][N:19]=1.[C-]#N.[Na+]>CS(C)=O.O>[CH:24]1([C:22]2[CH:21]=[CH:20][N:19]=[C:18]([C:8]#[N:1])[N:23]=2)[CH2:26][CH2:25]1

참가 물질

6

반응물 3

HCID 8929Sodium CyanideHCID 249019152-Chloro-4-cyclopropylpyrimidineHCID 66583054Diazabicyclooctane

생성물 1

HCID 670586444-Cyclopropylpyrimidine-2-carbonitrile수율 803.7%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매2회

실험 절차

To a solution of diazabicyclooctane (0.013 g, 0.12 mmol) in dimethylsulfoxide and water was added a solution of 2-chloro-4-cyclopropylpyrimidine (0.2 g, 1.2 mmol) in dimethylsulfoxide followed by sodium cyanide (0.066 g, 1.3 mmol). The reaction mixture was stirred at room temperature for 48 h. The mixture was then poured into water and extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The crude compound was purified via flash chromatography (10% ethyl acetate in petroleum ether) to afford 4-cyclopropylpyrimidine-2-carbonitrile (0.14 g, 77%). MS (ES+APCI) (M+H) 146.1; LCMS retention time 3.054 min (Method J).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified via flash chromatography (10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-aa4d59161afb4eefb0a4c12c62d8f791
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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