Potassium Bicarbonate → HCID 87556169, compound

HRID 2111359Notes

Reaction equation

HRID 2111359 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH3:2].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1.C(=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][N:7]([C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)[CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH3:2]

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 57635037HCID 57635037, compound

Product 1

HCID 87556169HCID 87556169, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 2.05 g (0.0095 mole) of (rac)-2-methyl-3-(tetrahydro-pyran-4-ylamino)-propanoic acid ethyl ester, 1.85 g (0.0095 mole) of 2,4-dichloro-5-nitro-pyrimidine 50 mL of ethyl acetate and 25 mL of water was added 2.85 g (0.0286 mole) of potassium bicarbonate. The mixture was stirred for 3 hours and then diluted with 50 mL of ethyl acetate and 50 mL of water. The layers were separated, and the aqueous layer extracted 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 hexanes-ethyl acetate (75:25) to give 3.48 g of (rac)-3-[(2-chloro-5-nitro-pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amino]-2-methyl-propanoic acid ethyl ester (IV-45) as pale yellow oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted 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 hexanes-ethyl acetate (75:25)

Sources & evidence

ORD record
ord-e05c855e679d41e49a01c3c96c7945f4
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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