Hydrochloric Acid → HCID 178481676, compound

HRID 1045674Notes

Reaction equation

HRID 1045674 reaction equation
C(O[C:4](=[O:20])[CH2:5][C:6](=O)[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]=1)C.[CH3:21][NH:22][C:23]([NH2:25])=[S:24].N12CCCN=C1CCCCC2.Cl>C(O)C>[SH:24][C:23]1[N:22]([CH3:21])[C:4](=[O:20])[CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:8]=2)[N:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723704MethylthioureaHCID 578700193-Oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester

Product 1

HCID 178481676HCID 178481676, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3-oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester (2.74 g, 10.1 mmol), N-methylthiourea (1.39 g, 15.5 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-en (1.57 g, 10.3 mmol) in ethanol (30 ml) was heated under reflux for 18 hours. After the solution was acidified by addition of hydrochloric acid, ethanol was removed under reduced pressure, and the resulting solid was filtered, washed with water and dried to afford 2-mercapto-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one (2.78 g, 93%).

Workup

  1. temperatureunder reflux for 18 hours
  2. customwas removed under reduced pressure
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f8f3e04793db47c2ad9eac4b63976e5b
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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