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

HRID 1671481Notes

Reaction equation

HRID 1671481 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. After removal of a half amount of ethanol under reduced pressure, hydrochloric acid was added to the solution. The resulting precipitate was collected by filtration, washed with water and then 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. customAfter removal of a half amount of ethanol under reduced pressure, hydrochloric acid
  2. additionwas added to the solution
  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-4a3a3ff3f43445f4a05cf3a44a360ac0
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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