Potassium Carbonate → HCID 57531550, compound

HRID 1091958Notes

Reaction equation

HRID 1091958 reaction equation
Cl[C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[C:6]([CH3:20])[N:5]=[C:4]([C:21]2[C:26]([CH2:27][CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:29][CH3:30])[N:3]=1.CC1(C)C(C)(C)OB([C:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH:40]=2)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:27]([C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:29][CH3:30])[C:21]=1[C:4]1[N:3]=[C:2]([C:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[CH2:41][CH:40]=2)[C:7]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=2[CH3:19])=[C:6]([CH3:20])[N:5]=1)[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 86602143HCID 86602143, compound

Product 1

HCID 57531550HCID 57531550, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-chloro-2-(2,6-diethylphenyl)-5-((5-isopropyl-2-methylphenoxy)methyl)-6-methylpyrimidine (423 mg, 1 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Wustrow and Wise, Synthesis, 1991, 993) (371 mg, 1.2 mmol) in anhydrous DMF (5 mL) is added K2CO3 (414 mg, 3 mmol). The mixture is bubbled with N2 for 15 min and PdCl2dppf (28 mg) is added. The mixture is then heated under N2 at 80° C. for 16 h. After cooling to room temperature, the mixture is diluted with ether, washed with water and brine. The organic layer is dried over anhydrous MgSO4, concentrated and purified by silica gel column chromatography to provide the title product. [mass expected (569.8); mass found (M+1: 570.6)].

Workup

  1. customThe mixture is bubbled with N2 for 15 min
  2. additionPdCl2dppf (28 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture is diluted with ether
  5. washwashed with water and brine
  6. dry with materialThe organic layer is dried over anhydrous MgSO4
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-7145acef9fcb4c2a968e068865770f55
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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