Cesium fluoride → HCID 68326551, compound

HRID 1400065Notes

Reaction equation

HRID 1400065 reaction equation
[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)OB([C:24]2[CH:29](C)[CH2:28][CH:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:26][CH:25]=2)O1.[F-].[Cs+]>O1CCOCC1.O.[Cl-].[NH4+]>[CH2:1]([C:8]1[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]=1[C:34]1[CH2:35][CH2:36][CH:31]([C:27]2[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=2)[CH2:32][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 23648513HCID 23648513, compoundHCID 86720800HCID 86720800, compound

Product 1

HCID 68326551HCID 68326551, compoundYield 31.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-benzyl-6-chloro-1H-pyrimidine-2,4-dione (WO06014394) (1.0 g), 4,4,5,6-tetramethyl-2-(4-phenylcyclohex-1-enyl)-[1,3,2]dioxaborolane (1.4 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (0.06 g) and cesium fluoride (1.92 g) in 1,4-dioxane (18 mL) and water (2 mL) was heated at 140° C. in a microwave reactor for 20 minutes. The resulting mixture was diluted with saturated aqueous ammonium chloride and filtered to remove the precipitate. The filtrate was extracted with dichloromethane and the combined organic layers washed with water and brine, then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume) to afford the title compound 2a as an off-white solid (0.48 g). LCMS (Method A): Rt=3.56 min. (M+H)+=359. 1H NMR (DMSO-D6): δ 11.06 (1 H, s), 10.69 (1 H, s), 7.23-7.21 (10 H, m), 5.84-5.79 (1 H, m), 3.61 (2 H, s), 3.57 (1 H, s), 2.77-2.67 (1 H, m), 2.19-2.16 (3 H, m), 1.84-1.81 (1 H, m), 1.68-1.67 (1 H, m).

Workup

  1. filtrationfiltered
  2. customto remove the precipitate
  3. extractionThe filtrate was extracted with dichloromethane
  4. washthe combined organic layers washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography on silica gel
  8. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:20 by volume)

Sources & evidence

ORD record
ord-7a070b7ac46d4c608d04fad0b2bee636
Source dataset
uspto-grants-2014_12
Patent number
US08906917B2

Reaction notes

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