Potassium Phosphate, Tribasic → HCID 56651722, compound

HRID 1464965Notes

Reaction equation

HRID 1464965 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[N:5]=[CH:4][N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:17]([N:19]1[CH2:24][CH2:23][NH:22][C:21](=[O:25])[CH2:20]1)=[O:18].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[C:6]([O:8][CH2:9][CH:10]([CH3:12])[CH3:11])[N:5]=[CH:4][N:3]=2)[C:21](=[O:25])[CH2:20]1)=[O:18]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 31097182HCID 31097182, compoundHCID 61278956HCID 61278956, compound

Product 1

HCID 56651722HCID 56651722, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-6-isobutoxypyrimidine (50 mg, 0.27 mmol), 4-(3-fluoro-4-methylbenzoyl)piperazin-2-one (76 mg, 0.32 mmol), tris(dibenzylideneacetone)dipalladium (12 mg, 0.013 mmol), Xantphos (23 mg, 0.040 mmol), and tripotassium phosphate (85 mg, 0.40 mmol) in dioxane (5 mL) was stirred at 100° C. for 12 h. After cooling to rt, the mixture was poured onto water, and the aqueous layer was extracted with dichloromethane (twice). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 4.3 mg (4% yields) of the title compound.

Workup

  1. temperatureAfter cooling to rt
  2. additionthe mixture was poured onto water
  3. extractionthe aqueous layer was extracted with dichloromethane (twice)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative LC-MS
  7. customto give

Sources & evidence

ORD record
ord-921bef34c1b348f4947c1293e7bebc5e
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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