N-bromobutanimide → HCID 58075473, compound

HRID 475852Notes

Reaction equation

HRID 475852 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])[CH:5]=[C:4]([NH:14][CH3:15])[N:3]=1.C1C(=O)N([Br:23])C(=O)C1>CC#N>[Br:23][C:5]1[C:6]([C:8]([N:10]([O:12][CH3:13])[CH3:11])=[O:9])=[N:7][C:2]([Cl:1])=[N:3][C:4]=1[NH:14][CH3:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58075693HCID 58075693, compound

Product 1

HCID 58075473HCID 58075473, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-N-methoxy-N-methyl-6-(methylamino)pyrimidine-4-carboxamide (959 mg) in MeCN (21 mL) was added NBS (814 mg), and the reaction mixture was heated at 60° C. for 8 h. The solvent was removed, and the residue was purified by Biotage eluting with 50%-70 EtOAc/Hexanes (1.2 L) to give the title compound as a white solid (1.1 g). LC-MS (M+H)+=310.95.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by Biotage
  3. washeluting with 50%-70 EtOAc/Hexanes (1.2 L)

Sources & evidence

ORD record
ord-65dc5f4e29bb47aaa6fbf66e41ae9821
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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