Cesium carbonate → HCID 90020504, compound

HRID 2200093Notes

Reaction equation

HRID 2200093 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH:18]1([C:21]([NH2:23])=[O:22])[CH2:20][CH2:19]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:23][C:21]([CH:18]3[CH2:20][CH2:19]3)=[O:22])[CH:7]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 634876Binap, (A+-)-HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidine

Product 1

HCID 90020504HCID 90020504, compoundYield 46.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Mix 4-chloro-6-(4-nitrophenoxyl)pyrimidine (10.6 g, 39.68 mmol), cyclopropanecarboxamide (8.7 g, 99.2 mmol) and 1,4-dioxane (150 mL). Then under N2, add tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 1.8 g, 1.98 mmol], (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 2.5 g, 3.97 mmol), Cs2CO3 (32 g, 99.5 mmol), and stir at 100° C. for 12 hrs. Cool to room temperature, filter, concentration and purification by chromatography (silica gel, DCM:EtOAc=1:5) afford the title compound (5.5 g, 43.6%). MS: (M+1): 301.

Workup

  1. temperatureCool to room temperature
  2. filtrationfilter
  3. concentrationconcentration and purification by chromatography (silica gel, DCM:EtOAc=1:5)

Sources & evidence

ORD record
ord-fe265f6ee938480b9a6ffa982fda3dcc
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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