Potassium Phosphate, Tribasic → HCID 57761903, compound

HRID 230953Notes

Reaction equation

HRID 230953 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:10][CH2:9]2)[N:5]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:3]=1.C[O:31][C:32]([CH2:34][CH2:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)=[O:33].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[N:24]1([C:4]2[N:3]=[C:2]([C:38]3[CH:37]=[C:36]([CH2:35][CH2:34][C:32]([OH:33])=[O:31])[CH:41]=[CH:40][CH:39]=3)[CH:7]=[C:6]([N:8]3[CH2:9][CH2:10][N:11]([C:14]4[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=4)[CH2:12][CH2:13]3)[N:5]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 4993880[3-(3-Methoxy-3-oxopropyl)phenyl]boronic acidHCID 57429019HCID 57429019, compound

Product 1

HCID 57761903HCID 57761903, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Purge a solution of 4-{4-chloro-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-yl}-morpholine (142 mg, 0.33 mmol), (3-(2-methoxycarbonylethyl)phenyl)boronic acid (Combi-Blocks, Inc., San Diego, Calif.; 104 mg, 0.5 mmol) and K3PO4 (2M, 331 μL) in dioxane with nitrogen for 10 minutes. Add Pd(PPh3)4 (19 mg, 0.017 mmol) and purge for an additional 5 minutes. Seal the contents in a reaction vial and heat at 80° C. for 16 hours. Partition the mixture between EtOAc and water, dry (Na2SO4) the organic layer and concentrate under reduced pressure. Filter the residue through a small pad of silica gel eluting with 50% EtOAc/hexanes. Concentrate under reduced pressure to give the title compound.

Workup

  1. customSeal the contents
  2. customin a reaction vial
  3. customPartition the mixture between EtOAc and water
  4. dry with materialdry (Na2SO4) the organic layer
  5. concentrationconcentrate under reduced pressure
  6. filtrationFilter the residue through a small pad of silica gel eluting with 50% EtOAc/hexanes
  7. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-85b1345fb92f4877b3a6ef0defd86eef
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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