Methanesulfonic Acid → 2-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-one

HRID 2245255Notes

Reaction equation

HRID 2245255 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][N:10]=1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][NH:16][C:17]([NH2:19])=[S:18].C1CCN2C(=NCCC2)CC1.CS(O)(=O)=O>C(O)C.O>[SH:18][C:17]1[N:16]([CH3:15])[C:4](=[O:6])[CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:19]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723704MethylthioureaHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate

Product 1

HCID 1784816782-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-oneYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-oxo-3-(4-pyrimidyl)propionate (34.1 g, 176 mmol), N-methylthiourea (47.5 g, 527 mmol) and 1,8-diazabicyclo[5,4,0]-7-undecene (26.3 ml, 176 mmol) in ethanol (340 ml) was refluxed for 2 hours and the solution of methanesulfonic acid (16.9 g, 176 mmol) in water (70 ml) was added after cooling by ice-water. The precipitate was washed with water, filtered and dried to give the title compound (30.2 g, 78%).

Workup

  1. washThe precipitate was washed with water
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-6e93d54155da4fc9a88e6c88f0b64eab
Source dataset
uspto-grants-2010_03
Patent number
US07683069B2

Reaction notes

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