2-Bromopropane → HCID 59256694, compound

HRID 640785Notes

Reaction equation

HRID 640785 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[Cl:5][C:6]1[C:15]2[C:10](=[C:11]([OH:16])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[N:7]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CS(C)=O>[Cl:5][C:6]1[C:15]2[C:10](=[C:11]([O:16][CH:2]([CH3:4])[CH3:3])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[N:7]=1

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 534265274-Chloro-2-methylquinazolin-8-ol

Product 1

HCID 59256694HCID 59256694, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromopropane (9 mmol) was added to a stirred mixture of 4-chloro-8-hydroxy-2-methyl-quinazoline (A2) (6 mmol), K2CO3 (24 mmol) and DMSO (20 mL). After 16 h at RT, saturated NH4Cl (20 mL) was added and the mixture extracted with dichloromethane (20 mL×3). The extracts were combined and concentrated. Diethyl ether (100 mL) was added to the residue and the resulting mixture washed successively with 2 N NaOH, H2O and brine, and dried (Na2SO4). Solvent removal afforded 4-chloro-8-isopropoxy-2-methyl-quinazoline (35) as a solid.

Workup

  1. extractionthe mixture extracted with dichloromethane (20 mL×3)
  2. concentrationconcentrated
  3. additionDiethyl ether (100 mL) was added to the residue
  4. washthe resulting mixture washed successively with 2 N NaOH, H2O and brine
  5. dry with materialdried (Na2SO4)
  6. customSolvent removal

Sources & evidence

ORD record
ord-c359dcf47a4a4925873e0e6e75be58b5
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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