N-bromobutanimide → HCID 178433331, compound

HRID 472215Notes

Reaction equation

HRID 472215 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-7257593b4c12487aa311a2e6350a433d
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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