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

HRID 1597249Notes

Reaction equation

HRID 1597249 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH:8]=[CH:9][CH2:10][OH:11])[CH2:3][CH2:2]1.O[C:13]1[CH:22]=[C:21]2[C:16]([C:17]([S:23][CH3:24])=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:24][S:23][C:17]1[C:16]2[C:21](=[CH:22][C:13]([O:11][CH2:10][CH:9]=[CH:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:14][CH:15]=2)[N:20]=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 539261284-Morpholinobut-2-en-1-olHCID 1356740197-Hydroxy4-methylsulphanylquinazoline

Product 1

HCID 536972334-Methylsulphanyl-7-(4-morpholinobut-2-en-1-yloxy)quinazolineYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a procedure analogous to the one described for the synthesis of the starting material in Example 16, 4-morpholinobut-2-en-1-ol (1.27 g, 8.13 mmol), (J. Med. Chem. 1972, 15, 110-112), was reacted with 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) in the presence of triphenylphosphine (4.09 g, 1.56 mmol) and diethyl azodicarboxylate (2.46 ml, 1.56 mmol) to give 4-methylsulphanyl-7-(4-morpholinobut-2-en-1-yloxy)quinazoline (1.15 g, 55%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-7ea7870dcb114cb8a9db38d038fdd17f
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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