Hydrochloric Acid → HCID 58154431, compound

HRID 2242028Notes

Reaction equation

HRID 2242028 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CS[C:16]1[N:21]=[C:20](O)[CH:19]=[CH:18][N:17]=1.O=P(Cl)(Cl)[Cl:25].Cl.O1CCOCC1>>[Cl:25][C:20]1[CH:19]=[CH:18][N:17]=[C:16]([NH:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:21]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 322853,4,5-TrimethoxyanilineHCID 178503462HCID 178503462, compound

Product 1

HCID 58154431HCID 58154431, compound

Conditions

Temperature
150 °C

Procedure

3,4,5-Trimethoxy-phenylamine (10 g, 54.6 mmol) and 2-methylsulfanyl-pyrimidin-4-ol (7.76 g, 54.6 mmol) are mixed and heated to 150° C. for 2 h whereupon the mixture melts. The evolving gas is absorbed in sodium hypochlorite solution. The remaining residue is suspended in acetonitrile (300 ml). POCl3 (10.8 ml, 117 mmol) and 4 N HCl in dioxane (35.2 ml, 140 mmol) are added and the mixture is heated to 90° C. until the reaction is complete. The mixture is extracted with ethyl acetate, washed with sat. sodium bicarbonate and brine. The organic layer is dried with sodium sulfate and evaporated. The residue is crystallized from methanol to give (4-chloro-pyrimidin-2-yl)-(3,4,5-trimethoxy-phenyl)-amine.

Workup

  1. customThe evolving gas is absorbed in sodium hypochlorite solution
  2. temperaturethe mixture is heated to 90° C. until the reaction
  3. extractionThe mixture is extracted with ethyl acetate
  4. washwashed with sat. sodium bicarbonate and brine
  5. dry with materialThe organic layer is dried with sodium sulfate
  6. customevaporated
  7. customThe residue is crystallized from methanol

Sources & evidence

ORD record
ord-976a25efaafb4b6aafa56d9c99cb52bc
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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