4-Methoxybenzylamine → HCID 22112737, compound

HRID 564874Notes

Reaction equation

HRID 564874 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[N:9]2)[CH:5]=[C:4](Cl)[N:3]=1.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1>O1CCCC1>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=[N:9]2)[CH:5]=[C:4]([NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)[N:3]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 18520372HCID 18520372, compound

Product 1

HCID 22112737HCID 22112737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture consisting of 3.0 g of ethyl 1-(2-amino-6-chloro-4-pyrimidinyl)-5-methyl-4-pyrazolecarboxylate, 3.5 ml of 4-methoxybenzylamine, and 150 ml of tetrahydrofuran was heated under reflux for 99 hours. The reaction mixture was cooled to room temperature and concentrated. Water was added to the residue, and the mixture was extracted three times with chloroform. The combined organic layers were washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography using a 49:1 mixture of chloroform and methanol as a developing solvent. The fraction containing the desired product was concentrated to afford 4.08 g of the title compound (amorphous).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 99 hours
  3. concentrationconcentrated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted three times with chloroform
  6. washThe combined organic layers were washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by evaporation
  9. customthe residue was purified by silica gel column chromatography
  10. additiona 49:1 mixture of chloroform and methanol as a developing solvent
  11. additionThe fraction containing the desired product
  12. concentrationwas concentrated

Sources & evidence

ORD record
ord-e11b3e43ba4e42b89f4daf755de35969
Source dataset
uspto-grants-2001_01
Patent number
US06169086A

Reaction notes

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