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

HRID 1275906

Reaction equation

HRID 1275906 reaction equation
[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:8]=3[CH:7]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[NH:22][CH:23]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:26].[CH2:27]([O:29][C:30]([C:32]1[O:33][C:34]([CH2:37]Br)=[CH:35][CH:36]=1)=[O:31])[CH3:28]>>[CH3:1][C:2]1[C:12]2[CH:11]=[CH:10][C:9]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:8]=3[CH:7]([C:18]3[C:19](=[O:25])[NH:20][C:21](=[O:24])[N:22]([CH2:37][C:34]4[O:33][C:32]([C:30]([O:29][CH2:27][CH3:28])=[O:31])=[CH:36][CH:35]=4)[CH:23]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:26]

Participants

3

Reactant 2

HCID 137895295-Bromomethyl-2-furancarboxylic acid ethyl esterHCID 22117215(+/-)-5-[1,2,8-Trimethyl-5H-dibenzo[a,d]cyclohepten-5-yl]-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 131722231(+/-)-5-[[3,4-Dihydro-5-{1,2,8-trimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-2-furancarboxylic acid, ethyl ester

Procedure

The subtitle compound was prepared from the product of step (v) (0.95 g) and 5-bromomethyl-2-furancarboxylic acid ethyl ester (J. Chem. Soc. Perkin Trans. 1, 1981, 1125, Bull. Chem. Soc. Jpn. 1987, 60, 1807)(0.64 g) according to the method of example 1 step (iv). Purification was by chromatography eluting with 20% ethyl acetate in toluene. Yield 1.02 g.

Workup

  1. customPurification
  2. washeluting with 20% ethyl acetate in toluene

Sources & evidence

ORD record
ord-965eb5b2f5714489bb2ddb2ab8110335
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Linked notes

Loading…