Methyl 3-(bromomethyl)benzoate → (+/-)-3-[[5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzoic acid, methyl ester

HRID 324413Notes

Reaction equation

HRID 324413 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1)[CH3:2].[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]Br)[CH:30]=1>>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:16]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[N:21]([CH2:35][C:31]4[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=4)[C:28]([O:27][CH3:26])=[O:37])[CH:22]=3)[C:11]3[N:12]=[C:13]([CH3:15])[O:14][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:25]=1)[CH3:2]

Participants

3

Reactant 2

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 70113435(+/-)-5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 131722509(+/-)-3-[[5-(7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]benzoic acid, methyl ester

Procedure

The subtitle compound was prepared from the product of example 3 step (vii) (2. g) and 3-bromomethyl benzoic acid methyl ester (0.5 g) using the method of example 1 step (viii). Purification was by chromatography eluting with 60% ethyl acetate in toluene.

Workup

  1. customPurification
  2. washeluting with 60% ethyl acetate in toluene

Sources & evidence

ORD record
ord-4eb3fca8a11941d2ab4eea3e461e6873
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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