Sodium Carbonate → 3-(4-Aminophenyl)-5-bromo-2-pyrazinamine

HRID 1853094Notes

Reaction equation

HRID 1853094 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[CH:20][C:21](N)=[N:22][CH:23]=2)O1.[C:26]([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1.O>[NH2:22][C:23]1[CH:18]=[CH:19][C:20]([C:2]2[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=2)=[CH:21][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6200042-Amino-3,5-dibromopyrazineHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 867248623-(4-Aminophenyl)-5-bromo-2-pyrazinamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

A suspension of 3,5-dibromopyrazin-2-amine (CAS No. 957230-70-5) (15 g), Pd(PPh3)4 (3.2 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (12 g), and Na2CO3 (12 g) in a 3 to 1 mixture of dioxane/water (600 mL) was degassed with a stream of nitrogen for 10 minutes. The reaction was heated at 90° C. overnight, at which time LC/MS indicated the reaction was complete. The mixture was concentrated, diluted with water (200 mL) and extracted with EtOAc (3×300 mL). The organic layers were combined, dried over Na2SO4, and evaporated under reduced pressure. The crude solid was triturated with a 1 to 1 mixture of DCM/MTBE (100 mL) to give the title compound (11 g) having the following physical data as a yellow solid.

Workup

  1. customwas degassed with a stream of nitrogen for 10 minutes
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water (200 mL)
  4. extractionextracted with EtOAc (3×300 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude solid was triturated with a 1 to 1 mixture of DCM/MTBE (100 mL)

Sources & evidence

ORD record
ord-09d7de0b411349c69c522b9c9af60898
Source dataset
uspto-grants-2015_02
Patent number
US08962623B2

Reaction notes

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