Triphenylphosphine → 7-(3-(1,1-Dioxothiomorpholino)propoxy)4-(2-methoxyethylsulphanyl)quinazoline

HRID 1597252Notes

Reaction equation

HRID 1597252 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([S:24][CH2:25][CH2:26][O:27][CH3:28])=[N:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1.[O:29]=[S:30]1(=[O:40])[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38]O)[CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[O:40]=[S:30]1(=[O:29])[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][O:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([S:24][CH2:25][CH2:26][O:27][CH3:28])=[N:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 114354734-(3-Hydroxypropyl)thiomorpholine 1,1-DioxideHCID 1357987517-Hydroxy-4-(2-methoxyethylsulphanyl)quinazoline

Product 1

HCID 694627627-(3-(1,1-Dioxothiomorpholino)propoxy)4-(2-methoxyethylsulphanyl)quinazolineYield 41.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (100 μl; 0.63 mmol) was added dropwise to a solution of 7-hydroxy-4-(2-methoxyethylsulphanyl)quinazoline (100 mg, 0.42 mmol), (prepared as described for the starting material in Example 11), 3-(1,1-dioxothiomorpholino)-1-propanol (99 mg, 0.51 mmol) and triphenylphosphine (167 mg, 0.63 mmol) in methylene chloride (6 ml). After stiring for 4 hours, triphenylphosphine (167 mg, 0.63 mmol) and diethyl azodicarboxylate (100 μl, 0.63 mmol) were added and stirring was continued for 1 hour. The volatiles were removed by evaporation and the residue was purified by column chromatography eluting with ethyl acetate/methanol (100/0 followed by 92/8). After removal of the solvent by evaporation, the residue was triturated with ether and the solid was collected by filtration and dried under vacuum to give 7-(3-(1,1-dioxothiomorpholino)propoxy)4-(2-methoxyethylsulphanyl)quinazoline (72 mg, 41%).

Workup

  1. custom(prepared
  2. waitwas continued for 1 hour
  3. customThe volatiles were removed by evaporation
  4. customthe residue was purified by column chromatography
  5. washeluting with ethyl acetate/methanol (100/0 followed by 92/8)
  6. customAfter removal of the solvent
  7. customby evaporation
  8. customthe residue was triturated with ether
  9. filtrationthe solid was collected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-5b08e7463a6d48068e245111785944e6
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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