Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate → HCID 25109217, compound

HRID 641615Notes

Reaction equation

HRID 641615 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].C1([C@H]2[O:40][CH:39]([CH2:41][O:42][NH2:43])[CH2:38][CH2:37][O:36]2)C=CC=CC=1>>[OH:40][C@H:39]([CH2:38][CH2:37][OH:36])[CH2:41][O:42][NH:43][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:21]

Participants

3

Reactant 2

HCID 59259226Phenyl 6-(2-fluoro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylateHCID 66624181HCID 66624181, compound

Product 1

HCID 25109217HCID 25109217, compoundYield 60%

Procedure

The title compound was synthesized following a similar procedure described in the synthesis of Example 2 by treatment of compound 2A with O-((R)-2-Phenyl-[1,3]dioxan-4-ylmethyl)-hydroxylamine, followed by acid hydrolysis of the resulting material (total yield 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.32 (s, 1 H) 11.97 (s, 1 H) 7.80 (dd, J=10.11, 1.77 Hz, 1 H) 7.58 (d, J=8.84 Hz, 1 H) 7.15 (t, J=8.59 Hz, 1 H) 4.90 (d, J=4.29 Hz, 1 H) 4.38 (t, J=5.05 Hz, 1 H) 3.71-3.90 (m, 2 H) 3.56-3.67 (m, 1 H) 3.44-3.53 (m, 2 H) 3.21 (s, 3 H) 2.96 (s, 3 H) 1.30-1.59 (m, 2 H). [M+H] calc'd for C17H20FIN4O6, 523; found, 523.

Workup

  1. customfollowed by acid hydrolysis of the resulting material (total yield 60%)

Sources & evidence

ORD record
ord-84ae9cb954ab421b87fbfb2f69fbaf6b
Source dataset
uspto-grants-2010_04
Patent number
US07696218B2

Reaction notes

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