Potassium Phosphate, Tribasic → HCID 57592511, compound

HRID 1784388Notes

Reaction equation

HRID 1784388 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:8]=2)[CH:6]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[OH:37].B(O)O>O1CCOCC1.CC(N(C)C)=O>[CH3:36][O:35][C:31]1[CH:32]=[C:33]([C:6]2[N:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[N:8]=3)[CH:4]=[N:3][CH:2]=2)[CH:34]=[C:29]([O:28][CH3:27])[C:30]=1[OH:37]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 57592522HCID 57592522, compoundHCID 178491379HCID 178491379, compound

Product 1

HCID 57592511HCID 57592511, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 4-[4-(4-Bromo-imidazol-1-yl)-pyrimidin-2-yl]-morpholine (0.20 g, 0.65 mmol) in anhydrous dioxane (6 ml) and anhydrous DMA (0.6 m) was added tripotassium phosphate (0.28 g, 1.3 mmol) and 2,6-dimethoxy-phenol-boronic acid (0.18 g, 0.91 mmol). The resultant mixture was degassed with sonication for 10 minutes before the addition of bis(tri-butylphospine)palladium (0.017 g, 0.033 mmol) and degassing for a further 5 minutes. The reaction vessel was sealed and heated under the influence of microwave radiation (170° C., 11 min, low absorption setting). Upon completion, the reaction was filtered through a thin silica plug which was then washed with 10% methanol/CH2Cl2. The filtrate was concentrated in vacuo and the crude residue purified by flash chromatography (SiO2) (1:1—EtOAc:Hexanes) to give the desired product (0.24 g, 96%) as a white crystalline solid in analytically pure form. m/z (LC-MSW, ESP):384.4 [M+H]+, R/T=2.72 mins.

Workup

  1. customdegassing for a further 5 minutes
  2. customThe reaction vessel was sealed
  3. filtrationUpon completion, the reaction was filtered through a thin silica plug which
  4. washwas then washed with 10% methanol/CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude residue purified by flash chromatography (SiO2) (1:1—EtOAc:Hexanes)

Sources & evidence

ORD record
ord-8d23601701674257bc08c9e2665decdf
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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