N-bromobutanimide → HCID 178496588, compound

HRID 472231Notes

Reaction equation

HRID 472231 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[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][CH3:20])[CH2:15][CH2:14]3)[C:6]=2[N:7]=1.[Br:22]N1C(=O)CCC1=O>CN(C)C=O.COC(C)(C)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:21])[C:5]2[CH:11]=[C:10]([Br:22])[C:9](=[O:12])[N:8]([C@H:13]3[CH2:14][CH2:15][C@H:16]([O:19][CH3:20])[CH2:17][CH2:18]3)[C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178496589HCID 178496589, compound

Product 1

HCID 178496588HCID 178496588, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-amino-8-(trans-4-methoxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (482 mg, 0.1.67 mmol) in dimethylformamide (15 mL) was added N-bromosuccinimide (300 mg, 1.69 mmol). After stirring for 1 hour at room temperature the solution was diluted with methyltertbutylether and washed with 50% sodium carbonate (2×) and brine. The combined aqueous layers were extracted with dichloromethane. The combined organics were dried (MgSO4) filtered and concentrated. The solids were triturated with diethyl ether to afford 2-amino-6-bromo-8-(trans-4-methoxycyclohexyl)-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (594 mg, 97%).

Workup

  1. washwashed with 50% sodium carbonate (2×) and brine
  2. extractionThe combined aqueous layers were extracted with dichloromethane
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solids were triturated with diethyl ether

Sources & evidence

ORD record
ord-d37bdaeacb9c456c8ecfa607a8f4c3a8
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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