Potassium Carbonate → 4-(6-Chloro-pyrimidin-4-yloxy)-2-methyl-6-nitro-phenylamine

HRID 1846452Notes

Reaction equation

HRID 1846452 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[CH:10][N:9]=1.[NH2:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([OH:25])=[CH:18][C:17]=1[CH3:26]>CN(C=O)C>[Cl:14][C:12]1[N:11]=[CH:10][N:9]=[C:8]([O:25][C:19]2[CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]([NH2:15])=[C:17]([CH3:26])[CH:18]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 709434,6-DichloropyrimidineHCID 669782964-Amino-3-methyl-5-nitrophenol

Product 1

HCID 866639074-(6-Chloro-pyrimidin-4-yloxy)-2-methyl-6-nitro-phenylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.66 g (12.0 mmol) potassium carbonate were added to 0.922 g (6.00 mmol) 4,6-dichloropyrimidine and 1.11 g (6.60 mmol) 4-amino-3-methyl-5-nitro-phenol in 1.5 mL DMF and the mixture was stirred for 6 h at 50° C. Then the mixture was added to ice water and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, evaporated down and purified by flash chromatography. The product-containing fractions were combined and evaporated down. The residue was triturated with EtOAc, suction filtered and dried under HV.

Workup

  1. extractionextracted several times with EtOAc
  2. customThe combined organic phases were dried on sodium sulphate
  3. customevaporated down
  4. custompurified by flash chromatography
  5. customevaporated down
  6. customThe residue was triturated with EtOAc, suction
  7. filtrationfiltered
  8. customdried under HV

Sources & evidence

ORD record
ord-1242765a086742be884edd4f3b8e7ebb
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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