Sodium Methoxide → HCID 11640716, compound

HRID 216193Notes

Reaction equation

HRID 216193 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[N:15]=[C:14](S(C)(=O)=O)[N:13]=2)[CH:6]=1)C.[CH3:36][O-:37].[Na+]>COCCOC>[CH3:1][O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[C:16]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[N:15]=[C:14]([O:37][CH3:36])[N:13]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69071657HCID 69071657, compound2×

Product 1

HCID 11640716HCID 11640716, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of above 3-{6-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-2-methanesulfonyl-pyrimidin-4-yloxy}-benzoic acid ethyl ester [180 mg, 0.36 mmol, Intermediate (72)] in 1,2-dimethoxyethane (5 mL) is added a 25% solution of sodium methoxide (3 mL). After 1 h at 20° C., the mixture is filtered through a plug of SiO2 (EtOAc). The filtrate is concentrated to give 3-{6-[2-(3,4-dimethoxy-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yloxy}-benzoic acid methyl ester [70 mg, 44%, Example (63)]. LCMS: RT=3.34 minutes, MS: 440 (M+H). IC50=6254 nM

Workup

  1. filtrationthe mixture is filtered through a plug of SiO2 (EtOAc)
  2. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-eaecbf56d8b648fba9014086f21fd1d6
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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