Dimethylamine → HCID 22402085, compound

HRID 2210245Notes

Reaction equation

HRID 2210245 reaction equation
CC1C=C2N=C(C)C=C(O)N2[N:3]=1.P(Cl)(Cl)([Cl:15])=O.CN(C)C1C=CC=CC=1.CNC.[CH3:30][C:31]1[CH:43]=[C:34]2[N:35]=[C:36]([CH3:42])[CH:37]=[C:38]([N:39]([CH3:41])[CH3:40])[N:33]2[N:32]=1>O.[C].[Pd].O.NN.C(O)C>[ClH:15].[NH2:3][C:43]1[C:31]([CH3:30])=[N:32][N:33]2[C:38]([N:39]([CH3:41])[CH3:40])=[CH:37][C:36]([CH3:42])=[N:35][C:34]=12

Participants

9

Reactant 5

HCID 674DimethylamineHCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 22402108N,N,2,5-Tetramethylpyrazolo[1,5-a]pyrimidin-7-amineHCID 178429164HCID 178429164, compound

Product 1

HCID 22402085HCID 22402085, compound

Reagents, catalysts & solvents 3

HCID 178514648HCID 178514648, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,5-Dimethyl-7-hydroxypyrazolo[1,5-a]-pyrimidine are heated under reflux for 40 minutes with 16.6 ml. phosphorus oxychloride and 0.8 ml. N,N-dimethylaniline. Excess phosphorus oxychloride is distilled off and the residue is poured on to ice. Extraction is carried out with methylene chloride, the organic phase is washed with an aqueous solution of sodium carbonate, dried and evaporated. The residue obtained is dissolved in 28 ml. ethanol and mixed with 2 g. of a 40% solution of dimethylamine in water. The mixture is stirred for 2.5 hours at ambient temperature, evaporated and the residue chromatographed over silica gel with ethyl acetate. There is obtained 0.86 g. (46% of theory) 2,5-dimethyl-7-(N,N-dimethylamino)pyrazolo[1,5-a]pyrimidine which is nitrosated analogously to Example 3. The nitroso compound is reduced analogously to Example 8 with palladium-carbon/hydrazine hydrate. There is obtained 0.8 g. of the title compound. Rf (silica gel, chloroform/methanol/methyl ethyl ketone/glacial acetic acid/water 75:35:25:5:8 v/v/v/v/v)-0.54.

Workup

  1. temperatureunder reflux for 40 minutes with 16.6 ml
  2. distillationExcess phosphorus oxychloride is distilled off
  3. additionthe residue is poured on to ice
  4. extractionExtraction
  5. washthe organic phase is washed with an aqueous solution of sodium carbonate
  6. customdried
  7. customevaporated
  8. customThe residue obtained
  9. dissolutionis dissolved in 28 ml
  10. customevaporated
  11. customthe residue chromatographed over silica gel with ethyl acetate
  12. customThere is obtained 0.86 g
  13. customThere is obtained 0.8 g

Sources & evidence

ORD record
ord-d65e19aac1244793acf0ba182925c66e
Source dataset
uspto-grants-1995_10
Patent number
US05457200

Reaction notes

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