N-bromobutanimide → HCID 178433331, compound

HRID 2389983Notes

Reaction equation

HRID 2389983 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:20])[C:5]2[CH:11]=[CH:10][C:9](=[O:12])[N:8]([C@H:13]3[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]3)[C:6]=2[N:7]=1.[Br:21]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:20])[C:5]2[CH:11]=[C:10]([Br:21])[C:9](=[O:12])[N:8]([C@H:13]3[CH2:14][CH2:15][C@H:16]([OH:19])[CH2:17][CH2:18]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178433337HCID 178433337, compound

Product 1

HCID 178433331HCID 178433331, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-8-(trans-4-hydroxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (115 mg, 0.419 mmol) in dimethylformamide (2.0 mL) was added N-bromosuccinimide (75 mg, 0.42 mmol). After stirring for 1.5 hr at room temperature the solution was concentrated. The residue was slurried in methanol, filtered solids, and the filtrated was concentrated and purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-3%). Combined solids to afford the title compound (120 mg, 81%).

Workup

  1. concentrationwas concentrated
  2. filtrationfiltered solids
  3. concentrationthe filtrated was concentrated
  4. custompurified by flash chromatography
  5. washeluting with chloroform/7 N ammonia in methanol (0.5-3%)

Sources & evidence

ORD record
ord-a2157170e14048efb1829ddb3e4fc23e
Source dataset
uspto-grants-2012_09
Patent number
US08273755B2

Reaction notes

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