Methyl iodide → Methyl alpha-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-beta-methoxyacrylate

HRID 2400123Notes

Reaction equation

HRID 2400123 reaction equation
C[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[C:5]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][N:3]=1.[H-].[Na+].[CH3:28]I.[CH:30]([O:32][CH3:33])=O>COCCOC.CCOCC>[CH3:28][C:4]1[N:3]=[CH:2][N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)[C:5]=1[C:21](=[CH:30][O:32][CH3:33])[C:22]([O:24][CH3:25])=[O:23]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 19044669Methyl alpha-[2-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate

Product 1

HCID 54403586Methyl alpha-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-beta-methoxyacrylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl α-[2-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate (8 mmol) are dissolved in methyl formate (10 ml) and added to a suspension of NaH (0.6 g, 80% in oil, 20 mmol) in 1,2-dimethoxyethane at room temperature. After 16 hours methyl iodide (2.5 ml, 40 mmol) is added with cooling. After further 2 hurs the reaction mixture is diluted with ether and washed with brine. Drying and chromatography on silicagel (eluent: hexane/ethlyacetate 1:1) gives the pure methyl α-[6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-β-methoxyacrylate as an oil.

Workup

  1. temperaturewith cooling
  2. washwashed with brine
  3. customDrying

Sources & evidence

ORD record
ord-1a51eb2998804c648a52877e26c86cfd
Source dataset
uspto-grants-1995_09
Patent number
US05453427

Reaction notes

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