Methyl chloroglyoxylate → 2-(6-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-oxoacetic acid

HRID 548794Notes

Reaction equation

HRID 548794 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]=1[C:20](OC1C=CC=CC=1)=[O:21].ClC(=O)[C:31]([O:33]C)=[O:32]>>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]=1[C:20](=[O:21])[C:31]([OH:33])=[O:32]

Participants

3

Reactant 2

HCID 79846Methyl chloroglyoxylateHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 251089582-(6-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-oxoacetic acid

Procedure

The title compound was synthesized following a similar procedure described in the synthesis of compound 2A from reaction of Example 1 with methyl 2-chloro-2-oxoacetate (hydrolysis of the crude upon column chromatography afforded Example 31). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.95 (s, 3H) 3.17 (s, 3H) 7.28 (s, 1H) 7.61 (m, 1H) 7.84 (m, 1H) [M+H] calc'd for C14H11FIN3O5, 448. found, 448.

Workup

  1. customhydrolysis of the crude upon column chromatography
  2. customafforded Example 31)

Sources & evidence

ORD record
ord-66158df885a24bb49c9a5cfe32d2e396
Source dataset
uspto-grants-2011_05
Patent number
US07943626B2

Reaction notes

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