HCID 178490494, compound → HCID 178489873, compound

HRID 403461Notes

Reaction equation

HRID 403461 reaction equation
[OH:1][C:2]1[C:7]([NH:8][C:9](=O)[C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH3:18])=[C:12]([CH3:19])[CH:11]=2)=[C:6]([OH:21])[N:5]=[C:4]([S:22][CH3:23])[N:3]=1>P(Cl)(Cl)(Cl)=O>[CH3:18][O:17][C:13]1[C:12]([CH3:19])=[CH:11][C:10]([C:9]2[O:21][C:6]3[N:5]=[C:4]([S:22][CH3:23])[N:3]=[C:2]([OH:1])[C:7]=3[N:8]=2)=[CH:15][C:14]=1[CH3:16]

Participants

3

Reactant 1

HCID 178490494HCID 178490494, compound

Product 1

HCID 178489873HCID 178489873, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

10.1 g of N-(4,6-dihydroxy-2-methylsulfanyl-pyrimidin-5-yl)-4-methoxy-3,5-dimethyl-benzamide in 55 ml of phosphorus oxychloride were heated to 60° C. for 3 h. After cooling, the resulting solid was collected by filtration with suction and washed with methyl tert-butyl ether. The solid was then dissolved in a mixture of dichloromethane and tetrahydrofuran, washed with a saturated aqueous sodium hydrogencarbonate solution, dried and concentrated in vacuo. 5.9 g of the title compound were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting solid was collected by filtration with suction
  3. washwashed with methyl tert-butyl ether
  4. dissolutionThe solid was then dissolved in a mixture of dichloromethane and tetrahydrofuran
  5. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95bb604427874cce8fe38a4875d6d1d9
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Reaction notes

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