Potassium Acetate → HCID 59514489, compound

HRID 1159653Notes

Reaction equation

HRID 1159653 reaction equation
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([N:13]([CH3:15])[CH3:14])[N:5]=[C:4]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[N:3]=1.C([O-])(=O)C.[K+]>CO.[Pd]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:4]2[N:5]=[C:6]([N:13]([CH3:15])[CH3:14])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:2][N:3]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 59514518HCID 59514518, compound

Product 1

HCID 59514489HCID 59514489, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl [4-chloro-6-(dimethylamino)-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (3.00 g, 8.22 mmol) and potassium acetate (2.42 g, 24.7 mmol) in methanol (30 mL) was treated with 10% Pd/C (1.00 g). The resulting black suspension was stirred under an atmosphere of hydrogen for 15 hours and then filtered over Celite. The residue was rinsed with methanol and the filtrate concentrated to dryness before partitioning between EtOAc and water. The separated organic layer was sequentially washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Chromatographic purification (silica gel, 1% MeOH in CHCl3) of the thus obtained crude product then yielded methyl [2-(4-aminobenzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (2.40 g, 97% yield) as a brown oil.

Workup

  1. filtrationfiltered over Celite
  2. washThe residue was rinsed with methanol
  3. concentrationthe filtrate concentrated to dryness
  4. custombefore partitioning between EtOAc and water
  5. washThe separated organic layer was sequentially washed with saturated NaHCO3 and brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customChromatographic purification (silica gel, 1% MeOH in CHCl3) of the
  10. customthus obtained crude product

Sources & evidence

ORD record
ord-705c782a9c3d4711b7c9a6dbfb993d70
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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