N-bromobutanimide → HCID 57929479, compound

HRID 2386689Notes

Reaction equation

HRID 2386689 reaction equation
[NH2:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12][CH3:13])=[N:7][C:6]=2[N:5]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[C:4](=[O:18])[CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[C:11]2[CH:10]=[N:9][C:8]([S:12][CH3:13])=[N:7][C:6]=2[N:5]([CH:14]2[CH2:17][CH2:16][CH2:15]2)[C:4](=[O:18])[C:3]=1[Br:19]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57929471HCID 57929471, compound

Product 1

HCID 57929479HCID 57929479, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-amino-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (1.3 g, 4.46 mmol) in DCM (120 mL) at 0° C. was added N-bromosuccinimide (0.87 g, 4.9 mmol) in 5 portions over 5 min. After stirring for 30 min, the DCM was evaporated under reduced pressure and the residue treated with 100 mL water and 100 mL NaHCO3 (sat'd, aq). The crude product was extracted into EtOAc (2×100 mL). The combined organic layers were washed with NaHCO3 (4×60 mL) and water (2×50 mL) and evaporated under reduced pressure to give 1.3 g of 5-amino-6-bromo-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a brown solid.

Workup

  1. customthe DCM was evaporated under reduced pressure
  2. additionthe residue treated with 100 mL water and 100 mL NaHCO3 (sat'd, aq)
  3. extractionThe crude product was extracted into EtOAc (2×100 mL)
  4. washThe combined organic layers were washed with NaHCO3 (4×60 mL) and water (2×50 mL)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c7f0c220db6144c0a8ef2441287689fe
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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