Guanidine → 7-bromoquinazolin-2-amine

HRID 2307801Notes

Reaction equation

HRID 2307801 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[NH2:11][C:12]([NH2:14])=[NH:13].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[N:11][C:12]([NH2:14])=[N:13]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 3520GuanidineHCID 6228DimethylformamideHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 107754847-bromoquinazolin-2-amineYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The 4-Bromo-2-fluoro-benzaldehyde (0.61 g, 3 mmol), guanidine (1.05 g, 5.83 mmol) and DMF were heated at 140° C. for 2.5 hours. 50 ml water was added to the mixture. The orange precipitate was filtered and washed with water. The solid was dissolved in 2N HCl. and filtered. The HCl solution was neutralized by ammonia hydroxyl. The off white solid was filtered and dried under vacuum to afforded the desired product (91 mg, 14%). MS (ESI) m/e 224 (M+1)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 7.00 (br. s., 2 H) 7.36 (d, J=8.82 Hz, 1 H) 7.77 (dd, J=9.16, 2.37 Hz, 1 H) 8.05 (d, J=2.37 Hz, 1 H) 9.09 (br. s., 1 H).

Workup

  1. filtrationThe orange precipitate was filtered
  2. washwashed with water
  3. dissolutionThe solid was dissolved in 2N HCl
  4. filtrationand filtered
  5. filtrationThe off white solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0e80b63316c64135a8352b023fccb35d
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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