Water → HCID 67298207, compound

HRID 1520387Notes

Reaction equation

HRID 1520387 reaction equation
[CH3:1][NH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[CH:11]=2)[N:6]=[C:5]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:4]=1.Br[CH2:27][CH2:28][Cl:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[Cl:29][CH2:28][CH2:27][O:19][C:15]1[CH:14]=[C:13]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]=[C:5]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[N:4]=[C:3]3[NH:2][CH3:1])[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 67297993HCID 67297993, compound

Product 1

HCID 67298207HCID 67298207, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol (0.30 g, 0.914 mmol), 1-bromo-2-chloroethane (0.38 ml, 4.57 mmol), and potassium carbonate (0.38 g, 2.74 mmol) in DMF (10 mL) was stirred for 2 days at room temperature. Water (10 mL) and ethyl acetate (10 mL) were added to the mixture and extracted. The organic layer was separated and concentrated in vacuo to leave a solid, which was collected by filtration and washed with hexane and dried to give 0.30 g of 6-(3-(2-chloroethoxy)phenyl)-N-methyl-2-(pyridin-3-yl)quinazolin-4-amine as brown solid (83%). The product was used without further purification.

Workup

  1. extractionextracted
  2. customThe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customto leave a solid, which
  5. filtrationwas collected by filtration
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-053e108af25646688298d2feed3a182c
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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