Potassium Carbonate → Methyl alpha-[4-(3-(2-cyanophenoxymethyl)-phenoxy)-6-methoxy-pyrimidin-5-yl]-beta-methoxyacrylate

HRID 1078197Notes

Reaction equation

HRID 1078197 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[O:6][C:7]1[C:12]([C:13](=[CH:18][O:19][CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[C:11]([O:21][CH3:22])[N:10]=[CH:9][N:8]=1.[OH:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:29]([C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[O:26][CH2:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[O:6][C:7]1[C:12]([C:13](=[CH:18][O:19][CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[C:11]([O:21][CH3:22])[N:10]=[CH:9][N:8]=1)#[N:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 53821122Methyl alpha-[4-(3-bromomethylphenoxy)-6-methoxy-5-pyrimidinyl]-beta-methoxyacrylate

Product 1

HCID 67742273Methyl alpha-[4-(3-(2-cyanophenoxymethyl)-phenoxy)-6-methoxy-pyrimidin-5-yl]-beta-methoxyacrylateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-[4-(3-bromomethylphenoxy)-6-methoxy-5-pyrimidinyl]-β-methoxyacrylate (3.2 g, 7.8 mmol), o-hydroxybenzonitril (0.93 g, 7.8 mmol) and potassium carbonate (2.1 g, 15 mmol) are stirred in dimethylformamide (20 ml) for 4 hours at room temperature. Dilution with ether, washing with brine, drying (MgSO4) and chromatography on silicagel (eluent: hexane/ethyl acetate 1:1) gives methyl α-[4-(3-(2-cyanophenoxymethyl)-phenoxy)-6-methoxy-pyrimidin-5-yl]-β-methoxyacrylate as a colorless solid (3.0 g), m.p. 132°-135° C.

Workup

  1. washDilution with ether, washing with brine
  2. dry with materialdrying (MgSO4) and chromatography on silicagel (eluent: hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-cf5b5640268248c6b7a2f042fe1421f1
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

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