Methyl alpha-[6-methyl-2-chloro-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate → Methyl [6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate

HRID 1682533Notes

Reaction equation

HRID 1682533 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=2)[C:3]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CO.CN(C)C.[Pd]>[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=2)[C:3]=1[CH2:22][C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 1

HCID 19044661Methyl alpha-[6-methyl-2-chloro-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate

Product 1

HCID 19044665Methyl [6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22022523Methanol trimethylamineSolvent

Procedure

Methyl α-[6-methyl-2-chloro-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate is dissolved in methanol/trimethylamine (50 ml/10 ml) and hydrogenated over Pd on charcoal (0.2 g). The reaction mixture is evaporated. Addition of potassium carbonate, ether extraction and chromatography on silica gel gives pure methyl α-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate. 1H (CDCl3):8.58 (s, 1H); 7.65-7.05 (m, 9H); 3.86 (s, 2H); 3.77 (s, 3H); 2.55 (s, 3H).

Workup

  1. customThe reaction mixture is evaporated
  2. additionAddition of potassium carbonate, ether extraction and chromatography on silica gel

Sources & evidence

ORD record
ord-b7649a1ea97e4d37b567e8090275e042
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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