N-bromobutanimide → HCID 178433332, compound

HRID 641701Notes

Reaction equation

HRID 641701 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:23])[C:5]2[CH:11]=[CH:10][C:9](=[O:12])[N:8]([C@H:13]3[CH2:18][CH2:17][C@@H:16]([O:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]3)[C:6]=2[N:7]=1.[Br:24]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:23])[C:5]2[CH:11]=[C:10]([Br:24])[C:9](=[O:12])[N:8]([C@H:13]3[CH2:14][CH2:15][C@@H:16]([O:19][CH2:20][CH2:21][OH:22])[CH2:17][CH2:18]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178433338HCID 178433338, compound

Product 1

HCID 178433332HCID 178433332, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-8-(cis-4-(2-hydroxyethoxy)cyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (411 mg, 1.29 mmol) in dimethylformamide (10 mL) was added N-bromosuccinimide (253 mg, 1.42 mmol). After stirring for 1 hour at room temperature the solution was concentrated. The residue was dissolved in chloroform (250 mL) and washed with 1 N sodium carbonate (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography eluting with 1:1 ethyl acetate:chloroform/7N ammonia in methanol (0-4%) to afford the title compound (382 mg, 75%).

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in chloroform (250 mL)
  3. washwashed with 1 N sodium carbonate (2×25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography
  8. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-ebc22f0cd5104b699eff561f0785bdcc
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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