Water → 2-[[3-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]methyl-methylamino]-5,6,7-trimethoxy-1H-quinazolin-4-one

HRID 1295733Notes

Reaction equation

HRID 1295733 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][NH:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].Cl[C:22]1[NH:23][C:24]2[C:29]([C:30](=[O:32])[N:31]=1)=[C:28]([O:33][CH3:34])[C:27]([O:35][CH3:36])=[C:26]([O:37][CH3:38])[CH:25]=2.CCN(CC)CC.O>CS(C)=O>[C:1]([Si:5]([CH3:19])([CH3:20])[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][N:14]([CH3:15])[C:22]1[NH:23][C:24]2[C:29]([C:30](=[O:32])[N:31]=1)=[C:28]([O:33][CH3:34])[C:27]([O:35][CH3:36])=[C:26]([O:37][CH3:38])[CH:25]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 69507752{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzyl}-methyl-amineHCID 1784868982-chloro-5,6,7-trimethoxy-1H-quinazolin-4-one

Product 1

HCID 1784869092-[[3-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]methyl-methylamino]-5,6,7-trimethoxy-1H-quinazolin-4-oneYield 82.12%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzyl}-methyl-amine from Step 3 (294 mg, 1.00 mmol) and 2-chloro-5,6,7-trimethoxy-1H-quinazolin-4-one (prepared as described previously) (270 mg, 1.00 mmol) were dissolved in dry DMSO. Et3N (0.14 mL, 1.00 mmol) was added and the mixture was heated to 120° C. overnight. Upon cooling, the mixture was poured into water and extracted with diethyl ether. The ethereal extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by SiO2 eluted with 99:1 CH2Cl2/MeOH to give 435 mg (82.12%) of a white crystalline solid.

Workup

  1. temperatureUpon cooling
  2. extractionextracted with diethyl ether
  3. dry with materialThe ethereal extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by SiO2
  6. washeluted with 99:1 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-99478206a0e1409f8afd8eaa98e6dbaa
Source dataset
uspto-grants-2007_07
Patent number
US07244738B2

Reaction notes

Loading…