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

HRID 2222247Notes

Reaction equation

HRID 2222247 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8d68b1b5470a4ab9a942f94bb7a57d7d
Source dataset
uspto-grants-2008_05
Patent number
US07371750B2

Reaction notes

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