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Cesium carbonate → HCID 57713942, compound

HRID 1984621
Notes
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Reaction equation

HRID 1984621 reaction equation
Cl[C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[N:13]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:12][S:11][C:8]1[N:9]=[CH:10][C:5]2[CH:4]=[C:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:2]([C:25]3[CH:26]=[CH:27][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=3)=[N:13][C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 5910734-Formylphenylboronic AcidHCID 577139437-Chloro-2-(methylsulfanyl)-6-phenylpyrido[2,3-d]pyrimidine

Product 1

HCID 57713942HCID 57713942, compound

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalyst
HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

The mixture of 7-chloro-2-(methylthio)-6-phenylpyrido[2,3-d]pyrimidine (0.100 g, 0.347 mmol), 4-formylphenylboronic acid (0.13 g, 0.87 mmol), Cesium carbonate (0.34 g, 1.04 mmol) and bis(tri-t-butylphosphine)palladium (0.018 g, 0.035 mmol) in dioxane (5 mL) was heated to reflux overnight. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel chromatography (20% EtOAc in hexane) to give the title compound. LRMS m/z (M+H) Calcd: 358.4, found: 358.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-8c44d7203cba40339e42984523d491ae
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07544677B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes