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

HRID 324396

Reaction equation

HRID 324396 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[NH:22][CH:23]=3)[C:6]=2[N:7]=1)[CH3:2].[CH2:26]([O:28][C:29]([C:31]1[N:32]=[C:33]([CH2:36]Br)[O:34][CH:35]=1)=[O:30])[CH3:27]>>[CH2:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:9]=3[CH:8]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[N:22]([CH2:36][C:33]4[O:34][CH:35]=[C:31]([C:29]([O:28][CH2:26][CH3:27])=[O:30])[N:32]=4)[CH:23]=3)[C:6]=2[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 641223Ethyl 2-(bromomethyl)-1,3-oxazole-4-carboxylateHCID 70112980(+/-)-5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 131722501(+/-)-2-[[5-(2-Ethyl-7-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-4-oxazolecarboxylic acid, ethyl ester

Procedure

The subtitle compound was prepared from the product from example 1 step (vii) (6.5 g) and 2-[bromomethyl]-4-oxazolecarboxylic acid ethyl ester (Coll. Czech Chem. Comm., 1967, 32, 2155) (1.69 g) by the method of example 1 step (viii). Purification was by chromatography eluting with 60-66% ethyl acetate in toluene.

Workup

  1. customPurification
  2. washeluting with 60-66% ethyl acetate in toluene

Sources & evidence

ORD record
ord-b60c5104cf494f52bcd926f4682ea92e
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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