Pyrrolidine → 3-Benzyloxy-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione

HRID 2270236Notes

Reaction equation

[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14](Cl)=[C:15]([F:20])[CH:16]=2)[N:11]([CH:22]2[CH2:24][CH2:23]2)[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C.Cl>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[C:15]([F:20])[CH:16]=2)[N:11]([CH:22]2[CH2:24][CH2:23]2)[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 3-benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione (Example E-3, 0.15 g, 0.42 mmol) in DMF (4.0 mL) was reacted with pyrrolidine (1.0 mL) and heated to 70° C. overnight. The mixture was then cooled, diluted with 0.25 M HCl, and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.15 g of the title compound as a solid.

Workup

temperatureThe mixture was then cooled
extractionextracted with ethyl acetate
dry with materialdried with sodium sulfate
concentrationconcentrated
customThe residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-b8002d216dc84861b66806e799ac89a3
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331538B1

Reaction notes

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