Cesium carbonate → HCID 58748738, compound

HRID 1662820Notes

Reaction equation

HRID 1662820 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].[N:11]1([CH2:16][CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][N:22]=2)=[O:20])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(Cl)Cl.CO>[N:11]1([CH2:16][CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([NH:10][C:7]3[N:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=3)=[CH:23][N:22]=2)=[O:20])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 764905-Nitropyrimidin-2-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 587487285-Bromo-pyridine-2-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide

Product 1

HCID 58748738HCID 58748738, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

In a dry 50 mL round bottom flask 5-nitro-pyrimidin-2-ylamine (0.2 g, 1.36 mmol), intermediate 21 (Example 29) (0.61 g, 2.04 mmol), cesium carbonate (1.33 g, 4.08 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.157 g, 0.272 mmol) and tris(dibenzylideneacetone) dipalladium (0.124 g, 0.136 mmol) were combined. Reactants were flushed with argon, diluted with dioxane (8 mL) and outfitted with reflux condenser. Reaction was heated to reflux for 18 h. Reaction was then filtered hot and solvents were evaporated to provide dark solids. Silica gel chromatography (6:1 DCM/MeOH) provided desired product as a yellow powder (0.17 g, 33% yield). Rf=0.23 (10% MeOH/DCM)

Workup

  1. customReactants were flushed with argon
  2. additiondiluted with dioxane (8 mL)
  3. temperaturewith reflux condenser
  4. customReaction
  5. temperaturewas heated
  6. temperatureto reflux for 18 h
  7. customReaction
  8. filtrationwas then filtered hot
  9. customsolvents were evaporated
  10. customto provide dark solids

Sources & evidence

ORD record
ord-4a63c764458a40a0ab0ce8cbf5ba8b32
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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