N-(2-aminoethyl)acetamide → N-{2-[(2-Chloro-5-nitropyrimidin-4-yl)amino]ethyl}acetamide

HRID 1443803Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[C:21]([NH:24][CH2:25][CH2:26][NH2:27])(=[O:23])[CH3:22]>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:27][CH2:26][CH2:25][NH:24][C:21](=[O:23])[CH3:22])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5.8 g (30 mmol) 2,4-dichloro-5-nitropyrimidine in 120 mL of tetrahydrofuran (THF) at −78° C. under Argon atmosphere was added 5.2 mL (30 mmol) of N,N-diisopropylethylamine followed by 3.1 mL (30 mmol) of N-acetylethylenediamine. The mixture was stirred at −78° C. for 30 min, allowed to warm to room temperature, and stirred for an additional 3 hours. The solvent was removed in vacuo and the residue purified by flash chromatography eluting with EtOAc to provide the compound of formula (2), N-(2-(2-chloro-5-nitropyrimidin-4-ylamino)ethyl)acetamide as pale yellow solid.

Workup

temperatureto warm to room temperature
stirringstirred for an additional 3 hours
customThe solvent was removed in vacuo
customthe residue purified by flash chromatography
washeluting with EtOAc

Sources & evidence

ORD record: ord-57703b16a929487f860dc7c2afda1fe5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662819B2

Reaction notes

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