Phenyl 6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate → N-(2-tert-butoxyethoxy)-6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

HRID 641601Notes

Reaction equation

HRID 641601 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].[C:29]([O:33][CH2:34][CH2:35][O:36][NH2:37])([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[C:29]([O:33][CH2:34][CH2:35][O:36][NH:37][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[Cl:1])=[O:21])([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 25108891Phenyl 6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylateHCID 46856370O-(2-tert-butoxyethyl)hydroxylamine

Product 1

HCID 25108892N-(2-tert-butoxyethoxy)-6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Phenyl 6-(2-chloro-4-iodophenylamino)-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (Example 23; 100 mg, 0.195 mmol, 1 eq) and O-(2-tert-butoxyethyl)hydroxylamine (See, WO05/110410; 260 mg, 1.95 mmol, 10 eq) were mixed in anhydrous THF (3 ml) and heated at 100° C. for 50 minutes in a microwave reactor. The protected product Example 24 was isolated by HPLC. [M+H] calc'd for C19H24ClIN4O5, 551; found, 551.

Workup

  1. customThe protected product Example 24 was isolated by HPLC

Sources & evidence

ORD record
ord-d1b20981e5d54cd39c6f9fb5e6f6b71e
Source dataset
uspto-grants-2010_04
Patent number
US07696218B2

Reaction notes

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