Triphenylphosphine → 4-Chloro-7-[3-(2,5-dioxoimidazolidin-1-yl)propoxy]-6-methoxyquinazoline

HRID 2068105Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.O[CH2:16][CH2:17][CH2:18][N:19]1[C:23](=[O:24])[CH2:22][NH:21][C:20]1=[O:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][CH2:18][N:19]3[C:23](=[O:24])[CH2:22][NH:21][C:20]3=[O:25])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-chloro-7-hydroxy-6-methoxyquinazoline (665 mg, 3.16 mmol), (prepared as described for the starting material in Example 4), 3-(3-hydroxypropyl)imidazolidine-2,4-dione (600 mg, 3.79 mmol) and triphenylphosphine in dichloromethane (15 ml) was stirred and cooled to 0° C. Diisopropyl azodicarboxylate (747 μl, 3.79 mmol) in dichloromethane (5 ml) was added and the mixture stirred at ambient temperature for 3 hours. Initially all material went into solution but later a precipitate formed. The mixture was concentrated and the solid residue suspended in methanol, filtered and dried in air to give 4-chloro-7-[3-(2,5-dioxoimidazolidin-1-yl)propoxy]-6-methoxyquinazoline (765 mg, 69%) as a pale yellow solid.

Workup

custom(prepared
stirringthe mixture stirred at ambient temperature for 3 hours
customlater a precipitate formed
concentrationThe mixture was concentrated
filtrationfiltered
customdried in air

Sources & evidence

ORD record: ord-7b58bdb7609146c3b24bfb7889ec6062
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293902B2

Reaction notes

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