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

HRID 2222247ノート

反応式

HRID 2222247 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 722075022-Chloro-4-(methylamino)-5-pyrimidinecarboxaldehyde収率 95%

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8d68b1b5470a4ab9a942f94bb7a57d7d
出典データセット
uspto-grants-2008_05
特許番号
US07371750B2

反応ノート

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