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

HRID 1988592ノート

反応式

HRID 1988592 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-423e9c97743244679c6cf840bae9b0ac
出典データセット
uspto-grants-2010_01
特許番号
US07642255B2

反応ノート

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