Water → tert-Butyl 4-{6-[3-(4-fluoro-phenyl)-prop-1-ynyl]-1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl}-benzoate

HRID 1062588Notes

Reaction equation

HRID 1062588 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:17][CH:16]=1)[C:5]2=[O:28].C(N(C(C)C)CC)(C)C.[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][C:46]#[CH:47])=[CH:41][CH:40]=1.O>CN(C=O)C.[Cu]I>[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][C:46]#[C:47][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][C:15]2[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[CH:17][CH:16]=2)[C:5]3=[O:28])=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 105586681-Fluoro-4-prop-2-ynyl-benzeneHCID 22281881tert-butyl 4-(6-iodo-1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoate

Product 1

HCID 10207080tert-Butyl 4-{6-[3-(4-fluoro-phenyl)-prop-1-ynyl]-1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl}-benzoate

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

To 1.0 g (2.0 mmol) 3-(3,4-Difluoro-benzyl)-6-iodo-1-methyl-1H-quinazoline-2,4-dione from Example 14 Step 1 and 1.0 g (8.4 mmol) di-isopropyl ethylamine in 15 ml DMF is added bis-triphenylphosphine palladium di-chloride (catalytic) followed by CuI (catalytic). 0.44 g (3.3 mmol) 1-fluoro-4-prop-2-ynyl-benzene is added and the mixture is heated to 70° C. for 6 hrs. The mixture is allowed to cool to room temperature and stir overnight. Water is added and the mixture stirred 30 minutes. Filtered and dry under reduced pressure.

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture stirred 30 minutes
  3. filtrationFiltered
  4. customdry under reduced pressure

Sources & evidence

ORD record
ord-34a806673baf4ee193b63817ce06dd88
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

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