1,2-Dimethoxyethane → HCID 59326982, compound

HRID 410323Notes

Reaction equation

HRID 410323 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl:9][C:10]1[C:15](I)=[CH:14][N:13]=[CH:12][N:11]=1.CC1(C)C(C)(C)OB([C:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:26]=2)O1.COCCOC>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:9][C:10]1[C:15]([C:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:26]=2)=[CH:14][N:13]=[CH:12][N:11]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 59326982HCID 59326982, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

To a sealable tube was added potassium phosphate (1.308 g, 6.16 mmol), dppf (0.051 g, 0.092 mmol), palladium (II) acetate (0.014 g, 0.062 mmol), 4-chloro-5-iodopyrimidine (0.741 g, 3.08 mmol), and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1 g, 3.23 mmol) followed by DME (17.60 mL) and water (2.93 mL) before sealing the reaction under argon and stirring at 85° C. for 4 h. It was cooled to room temperature and diluted with water before extracting with dichloromethane drying over magnesium sulfate, filtering, and concentrating under reduced pressure to a dark brownish-orange residue that was used without purification. MS (ESI, pos. ion) m/z: 296.2 (M+1).

Workup

  1. customthe reaction under argon
  2. temperatureIt was cooled to room temperature
  3. extractionbefore extracting with dichloromethane drying over magnesium sulfate
  4. filtrationfiltering
  5. concentrationconcentrating under reduced pressure to a dark brownish-orange residue that
  6. customwas used without purification

Sources & evidence

ORD record
ord-7c03eac3eace463c9e124a154a3d9b88
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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