Water → HCID 18455748, compound

HRID 1272496Notes

Reaction equation

HRID 1272496 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14].C(Cl)Cl.[OH2:18]>CN(C)C(=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]([C:7](=[O:14])[CH2:6][CH2:5][OH:18])[C:7]2=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 18455748HCID 18455748, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a suspension of NaH (60% in mineral oil, 199 mg) in 20 ml of N,N-dimethylacetamide was added 6-bromo-3H-quinazolin-4-one(0.9335 mg, 4.148 mmol). The mixture was stirred at room temperature for 40 mins resulting clear red solution. Acroyl chloride (471.8 ul, 5.8072 mmol) was added. The solution was heated at 70° C. for 8 hrs, cooled to room temperature, and poured into 30 ml of ice water. Methylene chloride added and product was in the water phase. The water solvent was evaporated under vacuum. The resulted residue was purified by preparative HPLC. 1.1 g product was obtained. Yield: 74.7%; 1H NMR (500 MHz, DMSO-d6): δ 2.73412–2.76135(t, J=6.805 Hz, 2H), 4.14197–4.16922(t, J=6.815 Hz, 2H), 7.62305–7.64046(d, J=8.705 Hz, 1H), 7.96596–7.98797(dd, J1=8.635 Hz, J2=2.38 Hz, 1H), 8.2287–8.2335(d, J=2.4 Hz, 1H), 8.41991(s, 1H); ESI-MS: m/z 297, 299 (M++1)

Workup

  1. customresulting clear red solution
  2. temperatureThe solution was heated at 70° C. for 8 hrs
  3. temperaturecooled to room temperature
  4. customThe water solvent was evaporated under vacuum
  5. customThe resulted residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-c958616f26a745d3a3ad18167ef75781
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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