5-Methylisoxazole-3-carbonyl chloride → 6-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-5-(5-methylisoxazole-3-carbonyl)pyrimidine-2,4(1H,3H)-dione

HRID 641607Notes

Reaction equation

HRID 641607 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].[CH3:29][C:30]1[O:34][N:33]=[C:32](C(Cl)=O)[CH:31]=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]([C:32]1[CH:31]=[C:30]([CH3:29])[O:34][N:33]=1)=[O:21]

Participants

3

Reactant 2

HCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 251089576-(2-Fluoro-4-iodophenylamino)-1,3-dimethyl-5-(5-methylisoxazole-3-carbonyl)pyrimidine-2,4(1H,3H)-dione

Procedure

The title compound was synthesized following a similar procedure described in the synthesis of compound 2A by reaction of Example 1 and 5-methylisoxazole-3-carbonyl chloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.42 (s, 2 H) 3.13 (s, 2 H) 3.19 (s, 2 H) 6.13-6.29 (m, 1 H) 7.08 (t, J=8.59 Hz, 1 H) 7.47 (dd, J=8.46, 1.89 Hz, 1 H) 7.68 (dd, J=9.98, 1.89 Hz, 1 H) 10.47 (s, 1 H) [M+H] calc'd for C17H14FIN4O4, 485; found, 485.

Sources & evidence

ORD record
ord-a28e566c5c56439c909a02065be0be19
Source dataset
uspto-grants-2010_04
Patent number
US07696218B2

Reaction notes

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