Cesium carbonate → HCID 70098861, compound

HRID 2368375Notes

Reaction equation

HRID 2368375 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([O:12][CH3:13])[N:6]=1)=[O:4].Br[C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=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>O1CCOCC1.C(#N)C.O.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.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH:11][C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)=[N:9][CH:8]=[C:7]([O:12][CH3:13])[N:6]=1)=[O:4]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 783445-BromopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16737663HCID 16737663, compound

Product 1

HCID 70098861HCID 70098861, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-amino-6-methoxypyrazine-2-carboxylic acid methyl ester (65 mg, 355 mmol), 5-bromopyrimidine (84.6 mg, 532 μmol) and cesium carbonate (162 mg, 497 μmol) in dioxane (1.5 ml) was treated with tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (36.7 mg, 35.5 μmol) and xantphos (67.8 mg, 117 μmol) under argon atmosphere and the reaction mixture was stirred at 110° C. for 16 h. After cooling down to ambient temperature, the reaction mixture was diluted with acetonitrile/water. The precipitated solid was sucked off, washed with acetonitrile/water, THF and MeOH and dried to yield the product as yellow solid (57 mg, 55.3%).

Workup

  1. temperatureAfter cooling down to ambient temperature
  2. washwashed with acetonitrile/water, THF and MeOH
  3. customdried

Sources & evidence

ORD record
ord-4e10bf0c210a45bcae5ac2aea73fa66c
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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