(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine → (R)-6-(2-chloro-4-iodophenylamino)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

HRID 641602Notes

Reaction equation

HRID 641602 reaction equation
[Cl: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([CH3:38])[O:34][C@@H:33]([CH2:35][O:36][NH2:37])[CH2:32][O:31]1>C1COCC1>[Cl: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]([NH:37][O:36][CH2:35][C@H:33]1[CH2:32][O:31][C:30]([CH3:38])([CH3:29])[O:34]1)=[O:21]

Participants

4

Reactant 2

HCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 25108891Phenyl 6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 25108894(R)-6-(2-chloro-4-iodophenylamino)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamideYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl 6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 23, 300 mg, 0.588 mmol, 1 eq) and (R)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine (260 mg, 1.826 mmol, 3 eq) were mixed in anhydrous THF (1.5 ml). The mixture was subjected to microwave irradiation at 100° C. for 50 minutes. The intended product was isolated by HPLC purification to give 140 mg of white solid (42%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (s, 3 H) 1.46 (s, 3 H) 3.04 (s, 3H) 3.38 (s, 3H) 3.85-3.8758 (m, J=8 Hz, 1 H) 4.03-4.05 (d, J=8 Hz, 2 H) 4.10-4.11 (t, J=4 Hz, 1 H) 6.70-6.72 (d, J=8 Hz, 1H) 7.56-7.58 (d, J=8 Hz,1 H) 7.82 (s, 1 H) 12.07 (s, 1 H) 12.79 (s, 1 H) [M+H] calc'd for C19H22ClIN4O6, 565; found, 565.

Workup

  1. customirradiation at 100° C. for 50 minutes
  2. customThe intended product was isolated by HPLC purification

Sources & evidence

ORD record
ord-10e0e57d6aca4cb582c2114228bfa907
Source dataset
uspto-grants-2010_04
Patent number
US07696218B2

Reaction notes

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