2-Fluoro-4-iodoaniline → HCID 24965727, compound

HRID 1660874Notes

Reaction equation

HRID 1660874 reaction equation
CC1C=CC(S(O[C:12]2[C:21]3[C:20](=[O:22])[N:19]([CH3:23])[CH:18]=[N:17][C:16]=3[N:15]([CH3:24])[C:14](=[O:25])[CH:13]=2)(=O)=O)=CC=1.[F:26][C:27]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:28]=1[NH2:29]>>[F:26][C:27]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:28]=1[NH:29][C:12]1[C:21]2[C:20](=[O:22])[N:19]([CH3:23])[CH:18]=[N:17][C:16]=2[N:15]([CH3:24])[C:14](=[O:25])[CH:13]=1

Participants

3

Reactant 2

HCID 1856942-Fluoro-4-iodoanilineHCID 59823038HCID 59823038, compound2×

Product 1

HCID 24965727HCID 24965727, compound

Procedure

3,8-dimethyl-4,7-dioxo-3,4,7,8-tetrahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzenesulfonate (compound 1D, 80 mg of 60% pure material) and 2-fluoro-4-iodoaniline (300 mg, large excess) were heated at 125° C. for 2 hours to yield 5-(2-fluoro-4-iodophenylamino)-3,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (Example 1). The product was confirmed by LC-MS and isolated by HPLC to give the title compound as a tan solid (17 mg). 1H NMR (400 MHz, MeOD) δ ppm 3.57 (s, 3H) 3.64 (s, 3H) 5.76 (s, 1H) 7.30 (t, J=8.34 Hz, 1H) 7.61 (dt, J=8.34, 1.01 Hz, 1H) 7.66 (dd, J=9.85, 1.77 Hz, 1H) 8.48 (s, 1H); [M+H] calc'd for C15H12FIN4O2, 427; found, 427.

Sources & evidence

ORD record
ord-82d0a913db434cf8be26966c3ab80d34
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

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