Methyl 5-(bromomethyl)furan-2-carboxylate → 5-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, methyl ester

HRID 1275883Notes

Reaction equation

HRID 1275883 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][C:26]([C:28]1[O:29][C:30]([CH2:33]Br)=[CH:31][CH:32]=1)=[O:27]>>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[N:20]([CH2:33][C:30]4[O:29][C:28]([C:26]([O:25][CH3:24])=[O:27])=[CH:32][CH:31]=4)[CH:21]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 1384229Methyl 5-(bromomethyl)furan-2-carboxylateHCID 110986755-(5h-Dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Product 1

HCID 867561245-[[5-{5H-Dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, methyl ester

Procedure

The subtitle compound was prepared from the product of example 1 step (iii) (1.1 g) and 5-bromomethyl-2-furancarboxylic acid methyl ester (0.96 g)(J. Chem. Soc. Perkin Trans. 1, 1981, 1125, Bull. Chem. Soc. Jpn. 1987, 60, 1807) according to the method of example 1 step (iv). Purification was by chromatography eluting with 50-80% ethyl acetate in isohexane. Yield 1.24 g.

Workup

  1. customPurification
  2. washeluting with 50-80% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-6624cdac8ba844f1858dd3a4b7dd5a47
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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