Cesium carbonate → 4-[2-(Ethylthio)-6-phenylpyrido[2,3-d]pyrimidine-7-yl]benzaldehyde

HRID 1984633Notes

Reaction equation

Cl[C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:4][C:5]2[CH:10]=[N:9][C:8]([S:11][CH2:12][CH3:13])=[N:7][C:6]=2[N:14]=1.[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].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>[CH2:12]([S:11][C:8]1[N:9]=[CH:10][C:5]2[CH:4]=[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:2]([C:26]3[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=3)=[N:14][C:6]=2[N:7]=1)[CH3:13]

Participants

Conditions

Temperature: 150 °C

Procedure

7-chloro-2-(methylthio)-6-phenylpyrido[2,3-d]pyrimidine (6-3) (0.80 g, 2.66 mmol) was combined with 4-formylphenylboronic acid (1.0 g, 6.64 mmol), cesium carbonate (4.30 g, 13 mmol), and bis(tri-t-butylphosphine)palladium (0.136 g, 0.266 mmol) in dioxane (10 mL) and heated in a microwave reactor at 150° C. for 60 min. The reaction mixture was diluted with water and extracted with CH2Cl2. he combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel chromatography (35% EtOAc in hexane) to give 4-[2-(ethylthio)-6-phenylpyrido[2,3-d]pyrimidine-7-yl]benzaldehyde. LRMS m/z (M+H) Calcd: 372.5, found: 372.5

Workup

extractionextracted with CH2Cl2
customwas dried
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (35% EtOAc in hexane)

Sources & evidence

ORD record: ord-852157233a194e5982eaf4114ef7138c
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544677B2

Reaction notes

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