Potassium Carbonate → HCID 58541888, compound

HRID 1966778Notes

Reaction equation

HRID 1966778 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][CH3:11])=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.[NH2:17][C:18]1[N:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.CCOC(C)=O.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>[CH3:12][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([C:21]2[CH:20]=[N:19][C:18]([NH2:17])=[N:23][CH:22]=2)=[CH:3][C:4]=1[N+:14]([O-:16])=[O:15])([CH3:13])[CH2:10][CH3:11]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 58542068HCID 58542068, compound

Product 1

HCID 58541888HCID 58541888, compoundYield 82.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture of crude (4-bromo-2-nitro-phenyl)-(1,1-dimethyl-propyl)-amine (600 mg, 2.09 mmol), 2-aminopyrimidine-5-boronic acid pinacol ester (330 mg, 1.49 mmol), Pd(PPh3)4 (160 mg), K2CO3 (600 mg, 4.34 mmol) in DMF (7.0 mL) and H2O (2.0 mL) is heated under microwave conditions at 100° C. for 1 hour. The reaction mixture is allowed to cool to room temperature, diluted with EtOAc (100 mL), washed with H2O (75 mL×2), dried with Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel flash column chromatography with 50% EtOAc in heptane as the eluent to afford 5-[4-(1,1-dimethyl-propylamino)-3-nitro-phenyl]-pyrimidin-2-ylamine (370 mg, 82%).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with H2O (75 mL×2)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customthe residue is purified by silica gel flash column chromatography with 50% EtOAc in heptane as the eluent

Sources & evidence

ORD record
ord-21a32d1914e448ddbe25517239d55810
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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