Nitrogen → HCID 86690310, compound

HRID 1521888Notes

Reaction equation

HRID 1521888 reaction equation
Br[C:2]1[C:3]([NH2:22])=[N:4][C:5]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:7]=1.N#N.C(N(CC)CC)C.[C:32]([CH:34]1[CH2:36][CH2:35]1)#[CH:33]>O1CCOCC1.[Cu]I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:34]1([C:32]#[C:33][C:2]2[C:3]([NH2:22])=[N:4][C:5]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[N:7]=2)[CH2:36][CH2:35]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 86690308HCID 86690308, compound

Product 1

HCID 86690310HCID 86690310, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-bromo-5,6-di-p-tolylpyrazin-2-amine (step 3) (440 mg, 1.24 mmol) in dioxane (5 ml) was degassed with N2 and treated with triethylamine (1.558 ml, 11.18 mmol), ethynylcyclopropane (0.210 ml, 2.484 mmol), copper(I) iodide (71.0 mg, 0.373 mmol) and PdCl2(dppf)-CH2Cl2-adduct (101 mg, 0.124 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated under reduced pressure and dry loaded onto silica using DCM (10 ml). Purification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the titled compound as a beige coloured solid;

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customdry
  3. customPurification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-9d604fdd9a7b4a1a81ee941b40e3a323
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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