Sodium Carbonate → HCID 70654899, compound

HRID 2091579Notes

Reaction equation

HRID 2091579 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)O1.C([O-])([O-])=O.[Na+].[Na+].Br[C:31]1[N:32]=[CH:33][C:34]([NH2:37])=[N:35][CH:36]=1>CCCCO.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>[NH2:37][C:34]1[N:35]=[CH:36][C:31]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3([C:21]#[N:22])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:13][CH:14]=2)=[N:32][CH:33]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 68572476HCID 68572476, compound

Product 1

HCID 70654899HCID 70654899, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile (1.53 g, 4.86 mmol), Pd(PPh3)4 (271 mg, 0.24 mmol), 2.0 M aq. Na2CO3 (4.9 mL) and the 5-bromopyrazin-2-amine (846 mg, 4.86 mmol) were combined in n-BuOH (20 mL). The slurry was degassed for 10 min under a bubbling stream of anhydrous nitrogen, then heated at 90° C. for 2 h. The resulting mixture was filtered, concentrated and purified by flash chromatography on silica (1-5% MeOH/DCM eluent) to provide 4-(4-(5-aminopyrazin-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile (1.08 g, 79% yield).

Workup

  1. customThe slurry was degassed for 10 min under a bubbling stream of anhydrous nitrogen
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated
  4. custompurified by flash chromatography on silica (1-5% MeOH/DCM eluent)

Sources & evidence

ORD record
ord-ca7c3c01835a4acba0b1b173c243d6fe
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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