Ethyl Acetate → HCID 57929469, compound

HRID 2386690Notes

Reaction equation

HRID 2386690 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])[C:3]=1Br.[Cu][C:21]#[N:22].C([O-])(O)=O.[Na+].CCOC(C)=O>CN1C(=O)CCC1>[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[C:21]#[N:22]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 57929479HCID 57929479, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 57929469HCID 57929469, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

To a solution of 5-amino-6-bromo-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (50 mg, 0.15 mmol) in 0.5 mL NMP was added copper(I) cyanide (56 mg, 0.63 mmol). The resulting mixture was heated at 220° C. in a microwave reactor for 20 min. After cooling, the reaction mixture was treated with a mixture of NaHCO3 (sat'd, aq) and EtOAc. The mixture was filtered and the collected solid then mixed with NH4OH (15%, aq). The aqueous mixture was extracted with EtOAc and then combined organic layers and evaporated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH, 93/7) to give 29 mg of 5-amino-6-cyano-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one as a solid.

Workup

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. additionthe collected solid then mixed with NH4OH (15%, aq)
  4. extractionThe aqueous mixture was extracted with EtOAc
  5. customcombined organic layers and evaporated under reduced pressure
  6. customThe crude residue was purified by preparative TLC (DCM/MeOH, 93/7)

Sources & evidence

ORD record
ord-eb1640c429d84298a23dc207ec3f9860
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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