HCID 178490494, compound → HCID 178489873, compound

HRID 81499Notes

Reaction equation

HRID 81499 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, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

10.1 g of N-(4,6-dihydroxy-2-methylsulfanylpyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamide in 55 ml of phosphorus oxychloride were heated at 60° C. for 3 h. After cooling, the solid obtained was filtered off with suction and washed with methyl tert-butyl ether. The solid was then dissolved in a mixture of dichloromethane and tetrahydrofuran, washed with saturated aqueous sodium bicarbonate solution, dried and concentrated under reduced pressure. This gave 5.9 g of the title compound. LC/MS (Method LC1): Rt=1.24 min; m/z=318.08 [M+H]+

Workup

  1. temperatureAfter cooling
  2. customthe solid obtained
  3. filtrationwas filtered off with suction
  4. washwashed with methyl tert-butyl ether
  5. dissolutionThe solid was then dissolved in a mixture of dichloromethane and tetrahydrofuran
  6. washwashed with saturated aqueous sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cc6ba24695f43dfb7836222e8398046
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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