4,6-Dichloro-5-nitropyrimidine → HCID 55035392, compound

HRID 629806Notes

Reaction equation

HRID 629806 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[Cl:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[C:14](Cl)[N:13]=[CH:12][N:11]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:14]1[C:15]([N+:16]([O-:18])=[O:17])=[C:10]([Cl:9])[N:11]=[CH:12][N:13]=1)[CH3:3]

Participants

5

Reactant 3

HCID 203124,6-Dichloro-5-nitropyrimidineHCID 81531DiisopropylethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 55035392HCID 55035392, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The amino-acetic acid ethyl ester hydrochloride (1439.15 mg; 10.31 mmol; 1.00 eq.) and 4,6-dichloro-5-nitro-pyrimidine (2000.00 mg; 10.31 mmol; 1.00 eq.) in anhydrous DMF (26 mL) was added ethyl-diisopropyl-amine (3997.72 mg; 30.93 mmol; 3.00 eq.) and the mixture was stirred for 3 hours. LC-MS showed that the reaction was complete. DMF was removed and EtOAc was added. The mixture was washed with brine, dried over MgSO4 and purified through flash chromatography on silica (EtOAc in Hexane from 0% to 30%) to provide (6-chloro-5-nitro-pyrimidin-4-ylamino)-acetic acid ethyl ester 2.1 g with 78% yield; LC/MS: 261 (M+H).

Workup

  1. customDMF was removed
  2. additionEtOAc was added
  3. washThe mixture was washed with brine
  4. dry with materialdried over MgSO4
  5. custompurified through flash chromatography on silica (EtOAc in Hexane from 0% to 30%)

Sources & evidence

ORD record
ord-ed00404515e848638053241226075025
Source dataset
uspto-grants-2016_04
Patent number
US09315517B2

Reaction notes

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