Potassium Carbonate → 5-(4-Tert-butylamino-3-nitro-phenyl)-pyrimidin-2-ylamine

HRID 1966666Notes

Reaction equation

HRID 1966666 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:25]=[N:26][C:27]([NH2:30])=[N:28][CH:29]=2)O1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)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>[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([C:24]2[CH:25]=[N:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[CH:3][C:4]=1[N+:13]([O-:15])=[O:14])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 467397914-bromo-N-(tert-butyl)-2-nitroaniline

Product 1

HCID 585420605-(4-Tert-butylamino-3-nitro-phenyl)-pyrimidin-2-ylamine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (4-bromo-2-nitro-phenyl)-tert-butyl-amine (7.2 g, 0.026 mol) in DMF (100 mL) and H2O (10 mL) are added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrimidin-2-ylamine (8.7 g, 0.04 mol), Pd(PPh3)4 (3 g, 0.003 mol) and K2CO3 (7.3 g, 0.053 mol) at room temperature. The solution is heated to 100° C. for 2 hours. The solution is cooled down, washed with H2O (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layer is dried with MgSO4 and filtered. The filtrate is concentrated and the residue is re-crystallized in CH2Cl2 (10 mL) to afford 5-(4-tert-butylamino-3-nitro-phenyl)-pyrimidin-2-ylamine as a scarlet solid (6.3 g, 83%).

Workup

  1. temperatureThe solution is cooled down
  2. washwashed with H2O (100 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layer is dried with MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is re-crystallized in CH2Cl2 (10 mL)

Sources & evidence

ORD record
ord-c00fd53f1cca49e28bdeebbb653a9b8f
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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