Methyl {4,6-dichloro-2-[(4-nitrophenyl)methyl]pyrimidin-5-yl}acetate → HCID 59514483, compound

HRID 1159656Notes

Reaction equation

HRID 1159656 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6]([Cl:13])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[N:3]=1>C1COCC1.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:4]2[N:5]=[C:6]([Cl:13])[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:2]([Cl:1])[N:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 50878583Methyl {4,6-dichloro-2-[(4-nitrophenyl)methyl]pyrimidin-5-yl}acetate

Product 1

HCID 59514483HCID 59514483, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl [4,6-dichloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.00 g, 5.62 mmol) in anhydrous THF (50 mL) was treated with Pd/C (10% Pd, 0.200 g) and the resulting black suspension was stirred under an atmosphere of hydrogen at room temperature. After 16 hours, the reaction mixture was filtered over Celite and the residue rinsed with copious amounts of MeOH. The filtrate was concentrated in vacuo to give the crude product as a dark yellow oil which was chromatographed (silica gel, 40% EtOAc in n-hexane) to give methyl [2-(4-aminobenzyl)-4,6-dichloropyrimidin-5-yl]acetate (1.32 g, 72% yield) as a white powder.

Workup

  1. filtrationthe reaction mixture was filtered over Celite
  2. washthe residue rinsed with copious amounts of MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give the crude product as a dark yellow oil which
  5. customwas chromatographed (silica gel, 40% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-9dd28a04ce804a9088ac3576cf5bd3c4
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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