Water → HCID 22281853, compound

HRID 1062590Notes

Reaction equation

HRID 1062590 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([I:22])[CH:18]=3)[N:13](C)[C:12]2=O)=[CH:6][CH:5]=1.C(N(C(C)C)CC)(C)C.C1(CC#C)C=CC=CC=1.O>CN(C=O)C.[Cu]I>[I:22][C:17]1[CH:16]=[CH:15][C:14]([NH:13][CH3:12])=[C:19]([CH:18]=1)[C:20]([NH:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:25])=[CH:5][CH:6]=1)=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 575753BenzylacetyleneHCID 11178438HCID 11178438, compound

Product 1

HCID 22281853HCID 22281853, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

To 19.6 g (44.9 mmol) 4-(6-Iodo-1-methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic acid methyl ester and 23.2 g (179.6 mmol) di-isopropyl ethylamine in 200 ml DMF is added bis-triphenylphosphine palladium di-chloride (1.0 g, catalytic) followed by CuI (0.4 g, catalytic). 7.3 g (62.9 mmol) 3-phenyl-propyne 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. Filter and dry under reduced pressure. Solid from EtOAc.

Workup

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

Sources & evidence

ORD record
ord-361911a6c1484771a6679eb7cf3c02ea
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

Loading…