Benzoyl Peroxide → 6-Bromomethyl-2,7-dimethyl-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-one

HRID 1198195Notes

Reaction equation

HRID 1198195 reaction equation
CC1NC(=O)C2C(=CC(C)=C(C)C=2)N=1.C(OCCl)(=O)C(C)(C)C.CC1NC(=O)C2C(=CC=C(C)C=2)N=1.[C:37]([O:43][CH2:44][N:45]1[C:54](=[O:55])[C:53]2[C:48](=[CH:49][C:50]([CH3:57])=[C:51]([CH3:56])[CH:52]=2)[N:47]=[C:46]1[CH3:58])(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39].[Br:59]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:59][CH2:56][C:51]1[CH:52]=[C:53]2[C:48](=[CH:49][C:50]=1[CH3:57])[N:47]=[C:46]([CH3:58])[N:45]([CH2:44][O:43][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C:54]2=[O:55]

Participants

7

Reactant 6

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 87885Chloromethyl pivalateHCID 117224573-(Pivaloyloxymethyl)-2,6,7-trimethyl-3,4-dihydroquinazolin-4-oneHCID 1355268562,6-dimethyl-4(3H)-quinazolinoneHCID 1355294132,6,7-Trimethylquinazolin-4(3H)-one

Product 1

HCID 104749406-Bromomethyl-2,7-dimethyl-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-oneYield 57%

Procedure

2,6,7-Trimethyl-3,4-dihydroquinazolin-4-one (European Patent Specification No. 0284338) was reacted with chloromethyl pivalate using the procedure described in European Patent Specification No. 0239362 for the corresponding reaction of 2,6-dimethyl-3,4-dihydroquinazolin-4-one. There was thus obtained 3-(pivaloyloxymethyl)-2,6,7-trimethyl-3,4-dihydroquinazolin-4-one. The product so obtained was reacted with N-bromosuccinimide in the presence of benzoyl peroxide using the procedure described in European Patent Specification No. 0284338 to give 6-bromomethyl-2,7-dimethyl-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-one in 57% yield, m.p. 149°-152° C.

Workup

  1. customThe product so obtained

Sources & evidence

ORD record
ord-93409bba142a4a5d978047adb955c496
Source dataset
uspto-grants-1994_01
Patent number
US05280027

Reaction notes

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