Nitrogen → HCID 86690309, compound

HRID 1521918Notes

Reaction equation

HRID 1521918 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1I.N#N.B(O)(O)[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[C:16]1([CH3:19])[CH:15]=[CH:14][C:13]([C:3]2[N:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 59457651HCID 59457651, compound

Product 1

HCID 86690309HCID 86690309, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 6-chloro-5-iodopyrazin-2-amine (step 1) (13.74 g, 53.8 mmol) in dioxane (300 ml) was degassed with N2 and treated with p-tolylboronic acid (17.55 g, 129 mmol), K2CO3 (22.30 g, 161 mmol) and PdCl2(dppf)-CH2Cl2-adduct (4.39 g, 5.38 mmol). The orange suspension was stirred at 110° C. for 2 days. After cooling to room temperature the reaction mixture was concentrated under reduced pressure. The crude mixture was absorbed onto silica and purification by chromatography eluting with 0-60% EtOAc in iso-hexane afforded the titled compound as a beige coloured solid;

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe crude mixture was absorbed onto silica and purification by chromatography
  4. washeluting with 0-60% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-dbb7b88f0b68436eba366b513cd829bc
Source dataset
uspto-grants-2015_07
Patent number
US09073932B2

Reaction notes

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