Potassium Carbonate → HCID 68991124, compound

HRID 657112Notes

Reaction equation

HRID 657112 reaction equation
Cl[C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=1.[CH3:21]B(O)O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 57928091HCID 57928091, compound

Product 1

HCID 68991124HCID 68991124, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

4-Chloro-2-[(E)-2-phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (0.434 g, 2.05 mmol) was dissolved in DMF (5 mL) and added to a microwave vial. MeB(OH)2 (0.273 g, 4.56 mmol), Pd(Ph3P)2Cl2 (0.107 g, 0.152 mmol) and K2CO3 (1.05 g, 7.61 mmol) were added and the vial was capped. The reaction was heated at 140° C. in the microwave for 10 minutes. The reaction was concentrated onto silica gel and purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired product as an off-white solid (0.431 g, 74%).

Workup

  1. additionadded to a microwave vial
  2. customthe vial was capped
  3. concentrationThe reaction was concentrated onto silica gel
  4. custompurified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-e4fe90b4f2eb4a8f8266ab020baa77d4
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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