Water → HCID 57870036, compound

HRID 1045675Notes

Reaction equation

HRID 1045675 reaction equation
S[C:2]1[N:3]([CH3:21])[C:4](=[O:20])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:9]=2)[N:7]=1.P(Cl)(Cl)([Cl:24])=O.O.C(=O)(O)[O-].[Na+]>ClCCCl.CN1CCCC1=O>[Cl:24][C:2]1[N:3]([CH3:21])[C:4](=[O:20])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:9]=2)[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178481676HCID 178481676, compound

Product 1

HCID 57870036HCID 57870036, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

2-Mercapto-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one (2.76 g, 9.33 mmol) in 1,2-dichloroethane (20 ml) and N-methylpyrrolidone (2 ml) was added to a solution of phosphorus oxychloride (3.83 g, 25.0 mmol) and N-methylpyrrolidone (5.22 g, 52.7 mmol) at 50° C. and the mixture was stirred for 20 minutes. The solution was poured into warm water, and sodium bicarbonate (10.2 g, 121 mmol) was added to the solution and the mixture was stirred until no gas was generated. The resulting solution was partitioned between water and dichloromethane, and the organic layer was washed with water and brine and passed through Celite. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1 to 1/1) to afford 2-chloro-1-methyl-2′-phenyl-1H-[4,4′]bipyrimidinyl-6-one (2.08 g, 75%).

Workup

  1. additionThe solution was poured
  2. additionwas added to the solution
  3. stirringthe mixture was stirred until no gas
  4. customThe resulting solution was partitioned between water and dichloromethane
  5. washthe organic layer was washed with water and brine
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-4d8759efc4d340f0bd3b1722c06236c4
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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