2-Amino-5-bromopyrimidine → HCID 115404597, compound

HRID 2203027Notes

Reaction equation

HRID 2203027 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.Br[CH:10]([CH3:16])[C:11]([CH:13]1[CH2:15][CH2:14]1)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([C:10]([CH3:16])=[C:11]([CH:13]3[CH2:15][CH2:14]3)[N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 2313102-Amino-5-bromopyrimidineHCID 450808052-Bromo-1-cyclopropylpropan-1-one

Product 1

HCID 115404597HCID 115404597, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopyrimidin-2-amine (500 mg) in DMF (10 ml) was added 2-bromo-1-cyclopropylpropan-1-one (1.02 g) at room temperature, and the mixture was stirred at 100° C. for 24 h. The mixture was partitioned between EtOAc and 1 M NaOH, and the organic layer was washed with 1 M NaOH and brine successively, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (89 mg) as yellow crystals.

Workup

  1. customThe mixture was partitioned between EtOAc and 1 M NaOH
  2. washthe organic layer was washed with 1 M NaOH and brine successively
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-5a85106a984749139cbe9325f58b4462
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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