Boron tribromide → 2-[3-(4-Hydroxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33971Notes

Reaction equation

HRID 33971 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:37])[CH2:11][NH:12][C:13]2[N:18]([CH3:19])[C:17](=[O:20])[C:16]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[C:15]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[N:14]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[2H]C([2H])([2H])C#N.[2H]O[2H]>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:37])[CH2:11][NH:12][C:13]2[N:18]([CH3:19])[C:17](=[O:20])[C:16]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=3)=[C:15]([C:31]3[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=3)[N:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 112488622-[3-(4-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-oneHCID 131725767CD3CN D2O

Product 1

HCID 115474272-[3-(4-Hydroxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a chilled (0° C.) stirring solution of 2-[3-(4-methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (250 mg, 0.21 mmol ) in 20 mL dichloromethane under an atmosphere of nitrogen was added boron tribromide (39 μL, 0.42 mmol) in 0.4 mL of dichloromethane. The resulting precipitate was stirred for 18 h warming to room temperature. The solvent was removed under reduced pressure, then the product was dissolved in 4 mL methanol. The product was purified on on reverse phase high performance chromatography eluting with a water/acetonitrile (0.1% TFA) gradient. The final product was lyophilized from 50% acetonitrile/water to give a yellow powder. M+1=477.2 NMR (CD3CN/D2O 3:1) s (3H, 3.40 ppm), s (2H, 3.60 ppm), s (2H, 4.25 ppm), d (2H, 6.51 ppm), d (2H, 6.95 ppm), d (1H, 7.22 ppm), m (3H, 7.4-7.5 ppm), d (2H, 7.5 ppm), d (1H, 7.72 ppm), d (1H, 7.78), d (2H, 8.30 ppm).

Workup

  1. temperaturewarming to room temperature
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe product was dissolved in 4 mL methanol
  4. customThe product was purified on on reverse phase high performance chromatography
  5. washeluting with a water/acetonitrile (0.1% TFA) gradient
  6. customto give a yellow powder

Sources & evidence

ORD record
ord-62d237e06bae4910b28fef51bd61684b
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

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