3-Mercaptopropionic Acid → 3-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]propionic acid

HRID 348438Notes

Reaction equation

HRID 348438 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.SC[CH2:22][C:23]([OH:25])=[O:24].C1CCN2C(=NCCC2)CC1>C1COCC1.C([O-])(O)=O.[Na+]>[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][CH2:19][CH2:22][C:23]([OH:25])=[O:24])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 65143-Mercaptopropionic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 210873953-[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]propionic acidYield 80.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (141 mg, 0.50 mmol) in THF (3 mL) was added 3-mercaptopropionic acid (88 μL, 1.0 mmol) followed by DBU (320 μL, 2.1 mmol). The solution was stirred for 25 min, diluted with 1% NaHCO3, and extracted with ethyl acetate. The aqueous layer was acidified with 3% HCl to afford a white precipitate. The solids were collected by filtration, washed with water and dried to afford 128.8 mg (79% yield) of the titled compound as a white solid. API-MS m/z 322 (MH+), 320 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate
  2. customto afford a white precipitate
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-fad343530eb9486e9fa100966d34dac7
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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