Dimethylformamide → HCID 59564548, compound

HRID 2096260Notes

Reaction equation

HRID 2096260 reaction equation
B1([C:10]2[CH:15]=[N:14][C:13]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:12][CH:11]=2)OC(C)(C)C(C)(C)O1.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1Br.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O>[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:10]1[CH:11]=[N:12][C:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 114141,2-DibromobenzeneHCID 164142134-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]morpholine

Product 1

HCID 59564548HCID 59564548, compoundYield 39.4%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

2-(4-Morpholino)pyrimidine-5-boronic acid pinacol ester (300 mg, 1.03 mmol), 1,2-dibromobenzene (243 mg, 1.03 mmol), Bis(triphenylphosphine)palladium (II) chloride (72 mg, 0.10 mmol), aqueous Na2CO3 (2N, 2.58 mL, 5.15 mmol) and DMF (5 mL) are added to a 10 mL microwave tube. Reaction is carried out in a microwave oven at 100° C. for 30 min. The reaction mixture turns black. The mixture is poured into water and extracted with EtOAc. The organic layers are washed with water, brine, dried (Na2SO4) and concentrated. The crude product is purified using biotage eluting with 0-30% EtOAc/Hexane. The desired mono-coupled product elutes at 30% EtOAc. The di-coupled by-product elutes earlier. Removal of the solvent gives 4-[5-(2-bromo-phenyl)-pyrimidin-2-yl]-morpholine as a white solid (130 mg, 39%).

Workup

  1. customReaction
  2. extractionextracted with EtOAc
  3. washThe organic layers are washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product is purified
  7. washeluting with 0-30% EtOAc/Hexane
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-f009be37482e4fe2b4b09a6cee8a5c7b
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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