Water → HCID 135995202, compound

HRID 1925020Notes

Reaction equation

HRID 1925020 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[C:9](=[O:15])[NH:10][C:11](=[O:14])[NH:12][CH:13]=2)[S:5][C:6]=1[CH3:7].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>N1C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[C:9](=[O:15])[N:10]([C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:23])[C:11](=[O:14])[NH:12][CH:13]=2)[S:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 135995200HCID 135995200, compound

Product 1

HCID 135995202HCID 135995202, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

(5-(4,5-dimethyl-1,3-thiazol-2-yl)-2,4(1H,3H)-pyrimidinedione) (Prep 15, 100 mg) suspended in Pyridine (2 mL) was slowly added to a stirring solution of benzoyl chloride (0.156 ml, 1.344 mmol) in Pyridine (1 mL) under nitrogen atmosphere. The resulting yellow solution was stirred at rt for 5.5 hours. Water was added (3 mL) and the mixture was extracted with EtOAc (10 mL). The organic was washed with NH4Cl saturated aqueous solution (2×2 mL) dried (Na2SO4, vacuo) to afford 340 mg of a yellowish solid that was dissolved in EtOAc (30 mL) and washed with NaHCO3 aqueous saturated solution. The organic was dried (Na2SO4, vacuo) to afford the title compound as a yellowish solid (180 mg)

Workup

  1. extractionthe mixture was extracted with EtOAc (10 mL)
  2. washThe organic was washed with NH4Cl saturated aqueous solution (2×2 mL)
  3. dry with materialdried (Na2SO4, vacuo)

Sources & evidence

ORD record
ord-4a0815e670374299a10de0c60520916a
Source dataset
uspto-grants-2012_05
Patent number
US08178549B2

Reaction notes

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