1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-one

HRID 1671487Notes

Reaction equation

HRID 1671487 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].N12CCCN=C1CCCCC2>C(O)C>[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

5

Reactant 3

HCID 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 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (36.10 g, 0.186 mol), N-methylthiourea (25.40 g, 0.282 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (29.11 g, 0.191 mol) in ethanol (150 ml) was refluxed for 21 hrs. A half amount of ethanol was evaporated under reduced pressure and hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with water and dried. The precipitate was stirred in hot ethyl acetate (1 L), and the precipitate was collected by filtration and dried to give 2-mercapto-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (33.91 g, 83%).

Workup

  1. customA half amount of ethanol was evaporated under reduced pressure and hydrochloric acid
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-207a473a72c3427a88ddd78cc411aa0e
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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