3-Fluoro-4-methoxyphenylboronic acid → 2-benzyl-5-(3-fluoro-4-methoxyphenyl)-3-methyl-3H-pyrimidin-4-one

HRID 1993342Notes

Reaction equation

HRID 1993342 reaction equation
[CH2:1]([C:8]1[N:13]([CH3:14])[C:12](=[O:15])[C:11](Br)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][C:20]=1[F:28]>C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.O.C(Cl)Cl.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>[CH2:1]([C:8]1[N:13]([CH3:14])[C:12](=[O:15])[C:11]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[C:20]([F:28])[CH:21]=2)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 2

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 574453912-benzyl-5-bromo-3-methylpyrimidin-4(3H)-one

Product 1

HCID 588288492-benzyl-5-(3-fluoro-4-methoxyphenyl)-3-methyl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Benzyl-5-bromo-3-methyl-3H-pyrimidin-4-one (Step 3, 11.1 g, 39.9 mmol), 4-methoxy-3-fluorophenylboronic acid (10.12 g, 59 mmol) and Pd(PPh3)4 (2.3 g, 1.9 mmol) in 2 M Na2CO3 (100 mL) and dioxane (150 mL) were heated to 90° C. for 1 h. The reaction was cooled to RT, and diluted with H2O and CH2Cl2. The organics were separated and washed with brine, dried (Na2SO4) and filtered through a plug of silica. The filtrate was concentrated under reduced pressure. Et2O/hexane (1:1) were added and the reaction was concentrated under vacuum to a brown solid. The solid was triturated with 20% Et2O/hexane to afford the title compound as a yellow solid. MS (ESI pos. ion) m/z: 325.2. Calc'd for C19H17FN2O2: 324.13.

Workup

  1. customThe organics were separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a plug of silica
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionEt2O/hexane (1:1) were added
  7. concentrationthe reaction was concentrated under vacuum to a brown solid
  8. customThe solid was triturated with 20% Et2O/hexane

Sources & evidence

ORD record
ord-609969a745ac4d5d83d9476c5f804698
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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