Potassium Bicarbonate → 3-[(2-Chloro-5-nitro-pyrimidin-4-yl)-(2-methoxy-ethyl)-amino]-propanoic acid tert-butyl ester

HRID 2111333Notes

Reaction equation

HRID 2111333 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][O:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][N:17]=1.C(=O)(O)[O-].[K+]>O.C(OCC)C>[C:1]([O:5][C:6](=[O:14])[CH2:7][CH2:8][N:9]([C:18]1[C:19]([N+:23]([O-:25])=[O:24])=[CH:20][N:21]=[C:16]([Cl:15])[N:17]=1)[CH2:10][CH2:11][O:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 42656843Tert-butyl 3-((2-methoxyethyl)amino)propanoate

Product 1

HCID 866234113-[(2-Chloro-5-nitro-pyrimidin-4-yl)-(2-methoxy-ethyl)-amino]-propanoic acid tert-butyl esterYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.23 g (0.011 mole) of 3-(2-methoxy-ethylamino)-propanoic acid tert-butyl ester in 20 mL of water was added dropwise to a solution of 1.94 g (0.01 mole) of 2,4-dichloro-5-nitro-pyrimidine in 20 mL of ethyl ether. At 0 degrees, 2.0 g (0.010 mole) of potassium bicarbonate was added. The mixture was stirred at ambient temperature for 3 hours. The layers were then separated, and the aqueous layer extracted twice with 30 mL of ether. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-85:15) gave 3.3 g of 3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(2-methoxy-ethyl)-amino]-propanoic acid tert-butyl ester (IV-40).

Workup

  1. customThe layers were then separated
  2. extractionthe aqueous layer extracted twice with 30 mL of ether
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-85:15)

Sources & evidence

ORD record
ord-b6d7c3e11f0f48fe84c9240cba6eb75c
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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