Triphenylphosphine → 4-Methylsulphanyl-7-(4-morpholinobut-2-yn-1-yloxy)quinazoline

HRID 1597248Notes

Reaction equation

HRID 1597248 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([S:31][CH3:32])=[N:26][CH:27]=[N:28]2)=[CH:23][CH:22]=1.[O:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]#[C:41][CH2:42]O)[CH2:35][CH2:34]1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:32][S:31][C:25]1[C:24]2[C:29](=[CH:30][C:21]([O:20][CH2:42][C:41]#[C:40][CH2:39][N:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)=[CH:22][CH:23]=2)[N:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 31128494-Morpholinobut-2-YN-1-OLHCID 1356740197-Hydroxy4-methylsulphanylquinazoline

Product 1

HCID 226492964-Methylsulphanyl-7-(4-morpholinobut-2-yn-1-yloxy)quinazolineYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (4.09 g, 1.56 mmol) was added dropwise to a solution of 7-hydroxy-4-methylsulphanylquinazoline (1.2 g, 6.25 mmol), (prepared as described for the starting material in Example 8), in methylene chloride (30 ml), followed by 4-morpholinobut-2-yn-1-ol (1.26 g, 8.3 mmol), (J. Am. Chem. Soc. 1957, 79, 6184), in methylene chloride (5 ml) and diethyl azodicarboxylate (2.46 ml, 1.56 mmol) was added dropwise. After stirring for 3 hours at ambient temperature, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with methylene chloride/methanol (100/0 followed by 95/5). After removal of the solvent, the residue was triturated with ether, collected by filtration and dried under vacuum to give 4-methylsulphanyl-7-(4-morpholinobut-2-yn-1-yloxy)quinazoline (1.3 g, 63%).

Workup

  1. custom(prepared
  2. additionwas added dropwise
  3. customthe volatiles were removed under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting with methylene chloride/methanol (100/0 followed by 95/5)
  6. customAfter removal of the solvent
  7. customthe residue was triturated with ether
  8. filtrationcollected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-15c47e07f5e145b5834ab978007c6088
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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