N,N'-Dimethylethylenediamine → HCID 11481143, compound

HRID 1883336Notes

Reaction equation

HRID 1883336 reaction equation
[CH:1]1([C:7]([NH2:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[N:13]1[CH:12]=[C:11]([NH:9][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[CH:16]=[N:15][CH:14]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 14283CyclohexanecarboxamideHCID 62657Potassium Phosphate, TribasicHCID 783445-Bromopyrimidine

Product 1

HCID 11481143HCID 11481143, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube containing a stirbar was charged with CuI (20 mg, 0.1 mmol, 10 mol %), cyclohexanecarboxamide (153 mg, 1.2 mmol), 5-bromopyrimidine (160 mg, 1 mmol), and K3PO4 (425 mg, 2 mmol), evacuated and backfilled with argon. N,N′-Dimethylethylenediamine (8.9 mg, 0.1 mmol) and dioxane (1 ml) were injected, and under a flow of argon, the septum was replaced by a Teflon screw cap. The tube was sealed, and the mixture was stirred and heated in an oil bath at 110° C. for 16 h. The contents of the tube were then partitioned between water and dichloromethane. The aqueous layer was separated, and extracted two times with additional dichloromethane. The organics were then combined, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue was chromatographed on silica gel followed by recrystallization from dichloromethane/hexane to give 154 mg (75%) of the title compound as a solid. 1H NMR (CDCl3, 300 MHz): δ 9.02 (s, 2H), 8.97 (s, 1H), 7.40 (br s, 1H), 2.32 (tt, 1H, J=3.6, 11.4 Hz), 2.10−1.20 (m, 10H).

Workup

  1. additionAn oven-dried resealable Schlenk tube containing a stirbar
  2. customevacuated
  3. customscrew cap
  4. customThe tube was sealed
  5. customThe contents of the tube were then partitioned between water and dichloromethane
  6. customThe aqueous layer was separated
  7. extractionextracted two times with additional dichloromethane
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was chromatographed on silica gel
  12. customfollowed by recrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-33ae5e7166484ad7aa4fce418854b82e
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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