Piperazine → HCID 178517383, compound

HRID 330847Notes

Reaction equation

HRID 330847 reaction equation
[OH-:1].[K+].[N:3]1([C:8]2[C:17]3[C:12](=[N:13][C:14](Cl)=[C:15]([Cl:18])[N:16]=3)[N:11]=[C:10](Cl)[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>O.O1CCCC1>[Cl:18][C:15]1[N:16]=[C:17]2[C:12](=[N:13][C:14]=1[OH:1])[N:11]=[C:10]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[N:9]=[C:8]2[N:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 4837PiperazineHCID 14797Potassium HydroxideHCID 137998844-Pyrrolidin-1-yl-2,6,7-trichloropteridine

Product 1

HCID 178517383HCID 178517383, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

a)+b) 460 μl (0.82 mmol) of a 10% solution of potassium hydroxide in water is added dropwise to a solution of 250 mg (0.82 mmol) 4-pyrrolidin-1-yl-2,6,7-trichloro-pteridine in 15 ml of tetrahydrofuran cooled to −10° C. The mixture is stirred for one hour at −10° C., slowly allowed to come up to ambient temperature and stirred for approx. another 16 hours. Then a solution of 318 mg (3.69 mmol) piperazine in 10 ml of tetrahydrofuran is added and the mixture is refluxed for approx. 16 hours. Then the solvent is eliminated in vacuo, the residue is mixed with water and extracted with dichloromethane. The organic phase is dried on sodium sulphate and the solvent is eliminated in vacuo. The residue is purified by chromatography. Yield 50 mg (14% of theoretical)

Workup

  1. customto come up to ambient temperature
  2. stirringstirred
  3. waitfor approx. another 16 hours
  4. temperaturethe mixture is refluxed for approx. 16 hours
  5. extractionextracted with dichloromethane
  6. customThe organic phase is dried on sodium sulphate
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-328cd6c9d5bf4080855c6d50cf864177
Source dataset
uspto-grants-2014_11
Patent number
US08877756B2

Reaction notes

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