Potassium Carbonate → HCID 24897293, compound

HRID 1920044Notes

Reaction equation

HRID 1920044 reaction equation
O[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[CH3:18])[N:5]=[C:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].P(Cl)(Cl)([Cl:33])=O>>[Cl:33][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=2[CH3:18])[N:5]=[C:4]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 178426705HCID 178426705, compound

Product 1

HCID 24897293HCID 24897293, compound

Conditions

Temperature
50 °C

Procedure

Under inert atmosphere, 27 g 6-hydroxy-N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine amine in 125 mL phosphorous oxychloride is suspended, and 11.5 g potassium carbonate is added portionwise. The mixture is heated to 50° C. for 6 hours under stirring. At the end of the reaction, the suspension is concentrated to residue, it is diluted with water, cooled, and the precipitate is filtrated. Upon drying, 26.6 g of product with HPLC purity of 80% (A %) is achieved, identified through LC-MS and 1H-NMR. Such raw product also contains a by-product, in an amount of about 15% (A %) which, during the following reduction reaction, still yields the desired product (4-methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine). The raw material, therefore, is employed as is in the example 13.

Workup

  1. customAt the end of the reaction
  2. concentrationthe suspension is concentrated to residue, it
  3. additionis diluted with water
  4. temperaturecooled
  5. filtrationthe precipitate is filtrated
  6. customUpon drying
  7. customin an amount of about 15% (A %) which, during the following reduction reaction

Sources & evidence

ORD record
ord-be54478c205849038167902197ce2388
Source dataset
uspto-grants-2012_05
Patent number
US08168787B2

Reaction notes

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