Dimethyl Sulfide → 2-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehyde

HRID 2222247노트

반응식

HRID 2222247 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:10]=C)=[CH:4][N:3]=1.[O:12]=[O+][O-].CSC>C(Cl)(Cl)Cl.CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([CH:10]=[O:12])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 714147842-Chloro-5-ethenyl-N-methylpyrimidin-4-amine

생성물 1

HCID 722075022-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehyde수율 95%

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

실험 절차

A solution of (2-chloro-5-vinyl-pyrimidin-4-yl)-methylamine (2.50 g, 14.7 mmol) in CHCl3/MeOH (15 mL/15 mL) is bubbled by ozone for 30 minutes and then passed by a stream of argon for 3 minutes at −78° C. The reaction mixture is allowed to warm up to room temperature and treated with dimethyl sulfide (3.24 mL, 44.1 mmol). The reaction mixture is concentrated under reduced pressure to give colorless oil that is purified by flash column chromatography (SiO2, EtOAc/Hx=1/3) over silica gel to give 2-chloro-4-methylamino-pyrimidine-5-carbaldehyde (2.40 g, 95%) as a white solid.

후처리

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto give colorless oil that
  3. customis purified by flash column chromatography (SiO2, EtOAc/Hx=1/3) over silica gel

출처 및 근거

ORD 기록
ord-8d68b1b5470a4ab9a942f94bb7a57d7d
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371750B2

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