Methyl 3-mercaptopropionate → 3-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]propionic acid methyl ester

HRID 348439Notes

Reaction equation

HRID 348439 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:17]([CH3:19])=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:26])[CH2:23]CS.C1CCN2C(=NCCC2)CC1>C1COCC1.C(OCC)(=O)C.CCCCCC>[CH3:20][O:21][C:22](=[O:26])[CH2:23][CH2:19][S:17][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

6

Reactant 3

HCID 18050Methyl 3-mercaptopropionateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 695234273-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]propionic acid methyl esterYield 58.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (50 mg, 0.18 mmol) in THF (0.9 mL) was added methyl-3-mercaptopropionate (40 μL, 0.36 mmol) followed by DBU (60 μL, 0.40 mmol). The solution was stirred for 1 h, diluted with 25% ethyl acetate/hexane and passed through a plug of SiO2 washing with 50% ethyl acetate/hexane. The filtrate was concentrated, and the resulting solids triturated with 20% ethyl acetate/hexane to afford 35.1 mg (58% yield) of the titled product as a white solid. ESI-MS m/z 336 (MH+), 334 (M−H)−.

Workup

  1. concentrationThe filtrate was concentrated
  2. customthe resulting solids triturated with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-81de815f92ae4bfb9852b83d7dc819b4
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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