Water → 2-Methyl-5-(1-piperazinyl)quinazoline

HRID 1179628Notes

Reaction equation

HRID 1179628 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2F)[N:3]=1.C(N(CC)CC)C.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.O>CN(C)C=O>[CH3:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 8471TriethylamineHCID 179651385-Fluoro-2-methylquinazoline

Product 1

HCID 574443582-Methyl-5-(1-piperazinyl)quinazolineYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 2-methyl-5-fluoro-quinazoline (WO02003068772, Chem. Abstr. 139:197493, 2 g; 12.3 mmol) in dry dimethylformamide (10 mL) were added triethylamine (3.4 mL; 2 eq) and piperazine (11 g; 10 eq). The reaction mixture was stirred under nitrogen at 120° C. for 4 h, then cooled to room temperature, poured into water (10 mL) and extracted with ethyl acetate (5×15 mL). The organic layers were combined, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by ion-exchange chromatography [SCX-2; MeOH -1M NH3/MeOH (1:0)→(0:1)] to afford the title compound as a yellow solid (1.8 g; yield 64%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (5×15 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by ion-exchange chromatography [SCX-2; MeOH -1M NH3/MeOH (1:0)→(0:1)]

Sources & evidence

ORD record
ord-a3da3cc5364c457db1bf71e08933484b
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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