Triphenylphosphine → 4-(2-Methoxyethylsulphanyl)-7-(3-methylsulphonylpropoxy)quinazoline

HRID 1597246Notes

Reaction equation

HRID 1597246 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([S:12][CH2:13][CH2:14][O:15][CH3:16])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][S:37]([CH2:40][CH2:41][CH2:42]O)(=[O:39])=[O:38].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:16][O:15][CH2:14][CH2:13][S:12][C:6]1[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:42][CH2:41][CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:3][CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2004243-(Methylsulfonyl)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1357987517-Hydroxy-4-(2-methoxyethylsulphanyl)quinazoline

Product 1

HCID 216992864-(2-Methoxyethylsulphanyl)-7-(3-methylsulphonylpropoxy)quinazolineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-hydroxy-4-(2-methoxyethylsulphanyl)quinazoline (0.1 g, 3.8 mmol) in methylene chloride (20nil) containing triphenylphosphine (1.7 g, 6.36 mmol), 3-(methylsulphonyl)-1-propanol (0.85 g, 6 mmol) and diethyl azodicarboxylate (1.05 ml, 6.36 mmol) was stirred for 3 hours at ambient temperature. After partial evaporation of the methylene chloride, ethyl acetate was added. The precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(2-methoxyethylsulphanyl)-7-(3-methylsulphonylpropoxy)quinazoline (960 mg, 71%).

Workup

  1. customAfter partial evaporation of the methylene chloride, ethyl acetate
  2. additionwas added
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-81d4c77dda104417b4bc2445d1d7ee01
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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