Cesium carbonate → HCID 66600037, compound

HRID 1621487Notes

Reaction equation

HRID 1621487 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=1.[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>[NH4+].[Cl-].[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[Cl:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 243561n-(6-chloro-2-methylpyrimidin-4-yl)acetamideHCID 447551543-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 66600037HCID 66600037, compoundYield 31.6%

Reagents, catalysts & solvents 3

HCID 178478230HCID 178478230, compoundCatalystHCID 962WaterSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(6-chloro-2-methylpyrimidin-4-yl)acetamide (228 mg, 1228 μmol), 3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (294 mg, 1228 μmol, Combi-Blocks, Inc., San Diego, Calif.), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (100 mg, 123 μmol), cesium carbonate (197 μl, 2457 μmol), dioxane (4 mL) and water (0.5 mL) was stirred at 100° C. for 30 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with EtOAc to give N-(6-(3-chloropyridin-4-yl)-2-methylpyrimidin-4-yl)acetamide (102 mg, 31.6% yield). 1H NMR (300 MHz, CDCl3) δ 8.80 (s, 1H); 8.56 (d, J=5.41 Hz, 1H); 8.34 (s, 1H); 7.94 (s, 1H); 7.44 (d, J=5.26 Hz, 1H); 2.69 (s, 3H); 2.25 (s, 3H). m/z (ESI, +ve ion) 263 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with EtOAc (2×30 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-e60df2746d1a4a78b4b091aa2244d9be
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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