Piperazine → 6-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-5-(piperazine-1-carbonyl)pyrimidine-2,4(1H,3H)-dione

HRID 548797Notes

Reaction equation

HRID 548797 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.[NH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[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]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:22]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 251090936-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-5-(piperazine-1-carbonyl)pyrimidine-2,4(1H,3H)-dione

Procedure

Example 43 was synthesized following a similar procedure described in the synthesis of Example 5 by reaction of compound 2A and piperazine. 1H NMR (400 MHz, CDCl3) δ 7.61 (d, J=8.0 Hz, 1H) 7.56 (d, J=8.0 Hz, 1H) 6.99 (t, J=8.0 Hz, 1H) 3.93 (m, 1H) 3.77 (m, 1H) 3.51 (s, 3H) 3.25 (s, 3H) 3.17 (m, 4H) 2.98 (m, 1H) 2.52 (m, 1H). [M+H] calc'd for C17H19FIN5O3, 488. found, 488.

Workup

  1. customExample 43 was synthesized

Sources & evidence

ORD record
ord-a9b160655f90459c9bebc31fc46b4a9e
Source dataset
uspto-grants-2011_05
Patent number
US07943626B2

Reaction notes

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