Cesium carbonate → HCID 67016438, compound

HRID 1919068Notes

Reaction equation

HRID 1919068 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][N:4]=1.Br[C:11]1[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=[C:15]([Br:17])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].O1CCOCC1>[Br:17][C:15]1[CH:16]=[C:11]([NH:9][C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[N:8]=2)[C:12](=[O:19])[N:13]([CH3:18])[CH:14]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1606792-O-MethylcytosineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-one

Product 1

HCID 67016438HCID 67016438, compoundYield 100.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Following Example 112a, 2-methoxypyrimidin-4-amine (0.625 g, 5 mmol), 3,5-dibromo-1-methyl-1H-pyridin-2-one (1.34 g, 5 mmol), cesium carbonate (4.88 g, 15 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.465 g, 0.5 mmol), Xantphos (0.58 g, 1 mmol) and 1,4-dioxane (50 mL) were heated at 100° C. for 24 hours. The mixture was cooled to room temperature, and filtered through a pad of Celite 521. The filter cake was washed with 9:1 methylene chloride/methanol (2×25 mL), and the combined filtrates were concentrated to dryness. The residue was dissolve in methylene chloride, diethyl ethyl was added, and the resulting precipitate was filtered to give a quantitative yield (1.57 g) of 263a as a green solid: MS (ESI+) m/z 313.1 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of Celite 521
  3. washThe filter cake was washed with 9:1 methylene chloride/methanol (2×25 mL)
  4. concentrationthe combined filtrates were concentrated to dryness
  5. dissolutionThe residue was dissolve in methylene chloride
  6. additiondiethyl ethyl was added
  7. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-3bb2f27680a440faa058b853983c0dd7
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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