Chlorosuccinimide → HCID 67047795, compound

HRID 1807374Notes

Reaction equation

HRID 1807374 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[N:8]=[C:7]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([Cl:19])=[CH:14][C:13]=2[F:20])[N:6]=1)=[O:4].[Cl:21]N1C(=O)CCC1=O>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:10]([Cl:21])=[C:9]([NH2:11])[N:8]=[C:7]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([Cl:19])=[CH:14][C:13]=2[F:20])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67048054HCID 67048054, compound

Product 1

HCID 67047795HCID 67047795, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

6-Amino-2-(4-chloro-2,5-difluorophenyl)pyrimidine-4-carboxylic acid methyl ester (0.090 g, 0.3 mmol) and N-chlorosuccinimide (0.05 g, 0.37 mmol) were combined in 10 mL acetonitrile and heated at 40° C. for 18 hours. The reaction mixture was concentrated and the product purified by column chromatography (ethyl acetate/hexane gradient) to yield the title compound as an off-white solid (0.050 g, 50% yield): 1H NMR (CDCl3): δ 7.85 (dd, 1H), 7.22 (dd, 1H), 5.62 (br s, 2H), 4.01 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product purified by column chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-c323d87e782c42128afa355366ab9830
Source dataset
uspto-grants-2013_01
Patent number
US08357633B2

Reaction notes

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