5-Bromomethyl-2-furancarboxylic acid ethyl ester → 5-[[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

HRID 1275890

Reaction equation

HRID 1275890 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[NH:20][CH:21]=3)[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.[CH2:26]([O:28][C:29]([C:31]1[O:32][C:33]([CH2:36]Br)=[CH:34][CH:35]=1)=[O:30])[CH3:27]>>[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[CH:6]([C:16]3[C:17](=[O:23])[NH:18][C:19](=[O:22])[N:20]([CH2:36][C:33]4[O:32][C:31]([C:29]([O:28][CH2:26][CH3:27])=[O:30])=[CH:35][CH:34]=4)[CH:21]=3)[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 137895295-Bromomethyl-2-furancarboxylic acid ethyl esterHCID 221172135-(2,8-Dimethyl-5h-dibenzo[a,d]cyclohepten-5-yl)-2,4(1h,3h)-pyrimidinedione

Product 1

HCID 867561265-[[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

Procedure

The subtitle compound was prepared from the product of example 8 step (i) (2.3 g) and 5-bromomethyl-2-furancarboxylic acid ethyl ester (J. Chem. Soc. Perkin Trans. 1, 1981, 1125, Bull. Chem. Soc. Jpn. 1987, 60, 1807) (2.3 g) according to the method of example 1 step (iv). Purification was by chromatography eluting with 25% ethyl acetate in toluene. Yield 1.8 g. Used directly in the next step.

Workup

  1. customPurification
  2. washeluting with 25% ethyl acetate in toluene

Sources & evidence

ORD record
ord-b5b1ba77ca1046f9b2325d9a5d96f2f1
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Linked notes

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