Ethylenediamine → N-(2-Aminoethyl)-6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

HRID 548796Notes

Reaction equation

HRID 548796 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]([O:22]C1C=CC=CC=1)=O.[CH2:29]([NH2:32])[CH2:30][NH2:31]>>[NH2:31][CH2:30][CH2:29][NH:32][C:20]([C:11]1[C:12](=[O:19])[N:13]([CH3:18])[C:14](=[O:17])[N:15]([CH3:16])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1])=[O:22]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 25109090N-(2-Aminoethyl)-6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

Procedure

Example 42 was synthesized following a similar procedure described in the synthesis of Example 5 by reaction of compound 2A and ethane-1,2-diamine. 1H NMR (400 MHz, CDCl3) δ 7.67 (d, J=8.0 Hz, 1H) 7.62 (d, J=8.0 Hz, 1H) 7.01 (t, J=8.0 Hz, 1H) 3.63 (t, J=4.0 Hz, 2H) 3.27 (s, 3H) 3.15 (t, J=4.0 Hz, 2H) 3.11 (s, 3H). [M+H] calc'd for C15H17FIN5O3, 462. found, 462.

Workup

  1. customExample 42 was synthesized

Sources & evidence

ORD record
ord-b611985c759d47b89f91bf8c2dacccaa
Source dataset
uspto-grants-2011_05
Patent number
US07943626B2

Reaction notes

Loading…