Methyl Glycolate → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl ester

HRID 348448Notes

Reaction equation

HRID 348448 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14](S(C)=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][OH:22].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:25][O:24][C:20](=[O:23])[CH2:21][O:22][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 66774Methyl GlycolateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 69522849[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl esterYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (prepared as in Example 1, 150 mg, 0.535 mmol) in THF (2 mL) was added methyl glycolate (82.5 μL, 1.07 mmol) followed by DBU (160 μL, 1.07 mmol). The reaction was stirred for 5 h, diluted with 3/6/1 ethyl acetate/hexane/dichloromethane, and passed through a plug of SiO2 using 4/5/1 ethyl acetate/hexane/dichloromethane. The filtrate was concentrated, and the resulting solids triturated with dichloromethane/hexane to afford 95.1 mg (58% yield) of the titled ester as a white solid. ESI-MS m/z 306 (MH+), 304 (M−H)−.

Workup

  1. concentrationThe filtrate was concentrated
  2. customthe resulting solids triturated with dichloromethane/hexane

Sources & evidence

ORD record
ord-a59f4340444544c9971f2ce9a86d9254
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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