Water → 6-Iodo-1-methylquinazoline-2,4(1H,3H)-dione

HRID 1062586Notes

Reaction equation

HRID 1062586 reaction equation
FC1C=C(C=CC=1F)C[N:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([I:17])[CH:13]=2)[N:8]([CH3:18])[C:7]1=[O:19].C(N(C(C)C)CC)(C)C.C1(CC#C)C=CC=CC=1.O>CN(C=O)C.[Cu]I>[I:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:18])[C:7](=[O:19])[NH:6][C:15]2=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 575753BenzylacetyleneHCID 22281861HCID 22281861, compound

Product 1

HCID 222818706-Iodo-1-methylquinazoline-2,4(1H,3H)-dione

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To 0.45 g (1.1 mmol) 3-(3,4-Difluoro-benzyl)-6-iodo-1-methyl-1H-quinazoline-2,4-dione and 0.56 g (4.4 mmol) di-isopropyl ethylamine in 15 ml DMF is added bis-triphenylphosphine palladium di-chloride (catalytic) followed by CuI (catalytic). 0.18 g (1.3 mmol) 3-phenyl-propyne is added and the mixture is heated to 70° C. for 6 hours. The mixture is allowed to cool to room temperature and stirred overnight. Water is added and the mixture stirred 30 minutes. Filtered and triturated solid in hot EtOAc and filtered. Purified by flash chromatography (EtOAc/hexane eluent).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture stirred 30 minutes
  3. filtrationFiltered
  4. customtriturated solid in hot EtOAc
  5. filtrationfiltered
  6. customPurified by flash chromatography (EtOAc/hexane eluent)

Sources & evidence

ORD record
ord-ed1b524242324f459348d6e56b4d954e
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

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