3-Hydroxyazetidine hydrochloride → 6-(2-Fluoro-4-iodo-phenylamino)-5-(3-hydroxy-azetidine-1-carbonyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione

HRID 548803Notes

Reaction equation

HRID 548803 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].Cl.[OH:30][CH:31]1[CH2:34][NH:33][CH2:32]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:33]1[CH2:34][CH:31]([OH:30])[CH2:32]1)=[O:21]

Participants

3

Reactant 2

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 251092196-(2-Fluoro-4-iodo-phenylamino)-5-(3-hydroxy-azetidine-1-carbonyl)-1,3-dimethyl-1H-pyrimidine-2,4-dioneYield 52%

Procedure

The title compound was synthesized from compound 2A and 3-hydroxyazetidine hydrochloride in 52% yield following a similar procedure described in the synthesis of Example 5. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.83 (s, 1H) 7.65 (d, J=9.85 Hz, 1H) 7.52 (d, J=9.60 Hz, 1H) 6.90-6.99 (m, 1H) 5.64 (d, J=5.31 Hz, 1H) 4.25-4.34 (m, 1H) 3.96-4.04 (m, 1H) 3.69-3.75 (m, 1H) 3.39-3.47 (m, 1H) 3.35 (s, 3H) 3.17-3.23 (m, 1H) 3.16 (s, 3H). [M+H] calc'd for C16H16FIN4O4, 475. found, 475.

Workup

  1. customdescribed in the synthesis of Example 5

Sources & evidence

ORD record
ord-019906d3de5940d1b3a7a8d5ed2afa6c
Source dataset
uspto-grants-2011_05
Patent number
US07943626B2

Reaction notes

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