Cesium carbonate → HCID 57929475, compound

HRID 2386691Notes

Reaction equation

HRID 2386691 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.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 57929479HCID 57929479, compound

Product 1

HCID 57929475HCID 57929475, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-amino-6-bromo-8-cyclobutyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (50 mg, 0.15 mmol), phenylboronic acid (28 mg, 0.22 mmol), tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) in 0.6 mL toluene and 0.6 mL EtOH was added cesium carbonate (0.17 g, 0.52 mmol). The resulting mixture was heated at 100° C. in a microwave reactor for 30 min. The reaction mixture was cooled, NaHCO3 (sat'd aq) added and the mixture extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×10 mL) and evaporated under reduced pressure. The crude residue was purified by preparative TLC (Hexanes:EtOAc, 2:1) to afford 40 mg of 5-amino-8-cyclobutyl-2-methylsulfanyl-6-phenyl-8H-pyrido[2,3-d]pyrimidin-7-one as a solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture extracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with water (2×10 mL)
  4. customevaporated under reduced pressure
  5. customThe crude residue was purified by preparative TLC (Hexanes:EtOAc, 2:1)

Sources & evidence

ORD record
ord-425cbc7c36564a74af853945be834793
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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