Cesium carbonate → 7-(4-Formylphenyl)-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile

HRID 1984625Notes

Reaction equation

HRID 1984625 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]([C:11]#[N: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.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>[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:3]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:4][C:5]3[CH:10]=[N:9][C:8]([C:11]#[N:12])=[N:7][C:6]=3[N:13]=2)=[CH:24][CH:23]=1)=[O:21]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 5910734-Formylphenylboronic AcidHCID 86078322HCID 86078322, compound

Product 1

HCID 860783257-(4-Formylphenyl)-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 7-chloro-6-phenylpyrido[2,3-d]pyrimidine-2-carbonitrile (2-4) (0.350 g, 1.31 mmol), 4-formylphenyl boronic acid (0.492 g, 3.28 mmol), cesium carbonate (1.28 g, 3.94 mmol), and Pd(PtBu3)2 (0.067 g, 0.131 mmol) in anhydrous dioxane (8 mL) was degassed (3× vacuum pump/refilled with N2) and heated to 95° C. for 18 hr. The mixture was cooled, diluted with water, and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. Purified by silica gel chromatography (10-30% EtOAc in Hexanes). 1H-NMR (500 MHz, CDCl3) δ 10.05 (s, 1H), 9.61 (s, 1H), 8.44 (s, 1H), 7.84 (d, 2H, J=8.3 Hz), 7.72 (d, 2H, J=8.3 Hz), 7.46-7.36 (m, 3H), 7.29-7.25 (m, 2H); LRMS, calc'd: 337.0, found: 337.0.

Workup

  1. customwas degassed
  2. addition(3× vacuum pump/refilled with N2)
  3. temperatureThe mixture was cooled
  4. additiondiluted with water
  5. extractionextracted 3× with CH2Cl2
  6. dry with materialThe combined organics were dried (anhd. Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurified by silica gel chromatography (10-30% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-3fdc7af3473c4eecad80b8570d7f11a6
Source dataset
uspto-grants-2009_06
Patent number
US07544677B2

Reaction notes

Loading…