Methanesulfonic Acid → HCID 178481675, compound

HRID 1091349Notes

Reaction equation

HRID 1091349 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[F:14])=O)C.[CH3:16][NH:17][C:18]([NH2:20])=[S:19].N12CCCN=C1CCCCC2.CS(O)(=O)=O>C1(C)C=CC=CC=1.O>[F:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:20]=[C:18]([SH:19])[N:17]([CH3:16])[C:4](=[O:3])[CH:5]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723704MethylthioureaHCID 59576754Ethyl 3-fluoro-beta-oxo-4-pyridinepropanoate

Product 1

HCID 178481675HCID 178481675, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(3-fluoropyridin-4-yl)-3-oxo-propionic acid ethyl ester (60.3 g, 286 mmol), N-methylthiourea (88 g, 976 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (48 g, 315 mmol) in toluene (600 ml) was heated at 100° C. for 5 hour. After addition of water (2000 ml) and methanesulfonic acid (30.3 g, 315 mmol) at room temperature and stirring for one hour, resulting precipitate was collected by filtration and dried to afford 6-(3-fluoropyridin-4-yl)-2-mercapto-3-methyl-3H-pyrimidin-4-one (46.3 g, 195 mmol, 68%) as white crystals.

Workup

  1. customresulting precipitate
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-ee1b90cc631a41bc80863838e2b82034
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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