Potassium Bicarbonate → HCID 87619359, compound

HRID 2111321Notes

Reaction equation

HRID 2111321 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH3:12])[CH2:5][NH:6][CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10].[Cl:14][C:15]1[N:20]=[C:19](Cl)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][N:16]=1.[C:25](=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[CH2:1]([O:2][C:3](=[O:13])[CH:4]([CH3:12])[CH2:5][N:6]([C:17]1[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][N:20]=[C:15]([Cl:14])[N:16]=1)[CH2:7][CH2:8][CH:9]([CH3:10])[CH3:11])[CH3:25]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 43398417HCID 43398417, compound

Product 1

HCID 87619359HCID 87619359, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 0.94 g (0.005 mole) of (rac)-2-methyl-3-(3-methyl-butylamino)-propanoic acid methyl ester, 0.97 g (0.005 mole) of 2,4-dichloro-5-nitro-pyrimidine, 25 mL of ethyl acetate and 12.5 mL of water was added 1.5 g (0.015 mole) of potassium bicarbonate. The mixture was stirred for 3 hours, then diluted with 50 mL of ethyl acetate and 50 mL of water. The layers were separated, and the aqueous layer was extracted with twice with 100 mL of ethyl acetate. The organic layers were washed with 100 mL of brine, combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-ethyl acetate (100:0-97:3) to give 1.06 g of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(3-methyl-butyl)-amino]-2-methyl-propanoic acid ethyl ester (IV-27) as a pale yellow oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with twice with 100 mL of ethyl acetate
  3. washThe organic layers were washed with 100 mL of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane-ethyl acetate (100:0-97:3)

Sources & evidence

ORD record
ord-fc4d5fe77d8f469c9ebb94ec83cefd73
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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