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2-Chlorobenzaldehyde → 5-(2-Chlorophenyl)-6-methoxycarbonyl-1,3-dimethyl-7-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,2,3,4,5,8-hexahydro-2,4-dioxopyrido[2,3-d]pyrimidine

HRID 981520
Notes
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Reaction equation

HRID 981520 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][C:11]1[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=[O:20])[CH:12]=1.[CH3:21][C:22]1[N:23]([CH2:29][CH2:30][O:31][CH2:32][C:33](=O)[CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:24]([CH3:28])=[C:25]([CH3:27])[N:26]=1>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:12]2[C:13](=[O:20])[N:14]([CH3:19])[C:15](=[O:18])[N:16]([CH3:17])[C:11]=2[NH:10][C:33]([CH2:32][O:31][CH2:30][CH2:29][N:23]2[C:24]([CH3:28])=[C:25]([CH3:27])[N:26]=[C:22]2[CH3:21])=[C:34]1[C:35]([O:37][CH3:38])=[O:36]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 811526-Amino-1,3-dimethyluracilHCID 20070375Methyl 4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]3-oxobutanoate

Product 1

HCID 200703655-(2-Chlorophenyl)-6-methoxycarbonyl-1,3-dimethyl-7-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,2,3,4,5,8-hexahydro-2,4-dioxopyrido[2,3-d]pyrimidineYield 4%

Procedure

The title compound (210 mg) was prepared from 2-chlorobenzaldehyde (1.4 g), 6-amino-1,3-dimethyl-2,4-dioxopyrimidine (1.55 g) and methyl 4-[2-(2,4,5-trimethylimidazol-1-yl)ethoxy]-3-oxobutanoate (2.68 g) by the method of Example 1. M.p. 226°-228° C.

Sources & evidence

ORD record
ord-49eaca29c46d446ca59fee64402b9f9d
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04992447

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes