Acetamidine → 7-Bromo-2-methylquinazoline

HRID 2307806Notes

Reaction equation

HRID 2307806 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[C:11]([NH2:14])(=[NH:13])[CH3:12]>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[N:13][C:11]([CH3:12])=[N:14]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67171AcetamidineHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 226078187-Bromo-2-methylquinazolineYield 4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

The 4-Bromo-2-fluoro-benzaldehyde (1 g, 4.9 mmol), acetamidine and DMA were mixed and heated to 140° C. for 5 hours. The mixture was cooled to room temperature and dried under vacuum. The mixture was purified by flash column afforded 47 mg product in 4% yield. MS (ESI) m/e 223 (M+1)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customdried under vacuum
  3. customThe mixture was purified by flash column

Sources & evidence

ORD record
ord-0e53fc394a054dc2b1c292595095782c
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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