Diisopropylethylamine → 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

HRID 394188Notes

Reaction equation

C(N(C(C)C)CC)(C)C.Br[C:11]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[C:36]([Br:43])[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34]C)=[CH:29][CH:28]=1)[C:15]([NH:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])=[O:16]>CN(C=O)C.[Cu]I>[Br:43][C:36]1[CH:37]=[C:38]([N+:40]([O-:42])=[O:41])[CH:39]=[C:11]2[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C:15](=[O:16])[N:17]2[C:18]1[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=1[Cl:24]

Participants

Conditions

Temperature: 130 °C

Procedure

Diisopropylethylamine (1.78 g, 13.8 mmol) and CuI (2.63 g, 13.8 mmol) was added to N-(2,6-dibromo-4-nitrobenzyl)-N′-(2,6-dichlorophenyl)-N-(4-ethoxybenzyl)urea (4.25 g, 6.88 mmol) in DMF (150 mL). After evacuating and flushing three times with argon, the reaction mixture was heated to 130° C. for 3 h, cooled to rt, and filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography on Biotage 40M columns, eluting with 80:20 hexanes-acetone to yield 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 536.0 (M+1).

Workup

customAfter evacuating
customflushing three times with argon
temperaturecooled to rt
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
custompurified by flash chromatography on Biotage 40M columns
washeluting with 80:20 hexanes-acetone

Sources & evidence

ORD record: ord-797a6050d93b4dbd846880fffb77b996
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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