Sodium Carbonate → HCID 68107226, compound

HRID 2403576Notes

Reaction equation

HRID 2403576 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][C@H:12]([CH3:14])[O:11][C@H:10]([CH3:15])[CH2:9]2)=[N:6][CH:7]=1.[CH3:16][N:17]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=1)[C:18](=[O:28])[CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C@H:10]1[O:11][C@@H:12]([CH3:14])[CH2:13][N:8]([C:5]2[N:4]=[CH:3][C:2]([C:32]3[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=3)[CH2:29][N:17]([CH3:16])[C:18](=[O:28])[CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[CH:7][N:6]=2)[CH2:9]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 59292265HCID 59292265, compoundHCID 70571759HCID 70571759, compound

Product 1

HCID 68107226HCID 68107226, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

rel-(2R,6S)-4-(5-Bromopyrimidin-2-yl)-2,6-dimethylmorpholine (118 mg) and tert-butyl (2-{methyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]amino}-2-oxoethyl)carbamate (175 mg) were dissolved in DME (2 ml) and water (1 ml), and tetrakis(triphenylphosphine)palladium (15 mg) and sodium carbonate (137 mg) were added thereto, followed by stirring at 80° C. for 24 hours. The obtained residue was subjected to liquid separation with CHCl3 and water. The organic layer was separated, and then the aqueous layer was extracted with CHCl3 again. These organic layers were combined, dried over Na2SO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3) to obtain tert-butyl rel-{2-[(3-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]pyrimidin-5-yl}benzyl)(methyl)amino]-2-oxoethyl]carbamate (190 mg) as a colorless oil.

Workup

  1. customThe obtained residue was subjected to liquid separation with CHCl3 and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CHCl3 again
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (2% MeOH/CHCl3)

Sources & evidence

ORD record
ord-24d3ac73a237464ba20c7344539259a9
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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