Pyrrolidine → HCID 18326543, compound

HRID 1250664Notes

Reaction equation

HRID 1250664 reaction equation
[C:1]([O:5]C(OC(OC(C)(C)C)=O)=O)(C)(C)C.[CH2:16]([NH:19][C:20]1[N:21]=[C:22]([NH2:30])[C:23]2[S:28][CH:27]=[C:26]([CH3:29])[C:24]=2[N:25]=1)[CH:17]=[CH2:18].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(OCC)(=O)C.CCCCCC>C(#N)C>[CH2:16]([NH:19][C:20]1[N:21]=[C:22]([NH:30][C:1]([N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:5])[C:23]2[S:28][CH:27]=[C:26]([CH3:29])[C:24]=2[N:25]=1)[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 90495Di-tert-butyl dicarbonateHCID 18326385HCID 18326385, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18326543HCID 18326543, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

122 mg (1.0 mmol) of N,N-dimethylaminopyridine was added to a solution of 306 mg (1.4 mmol) of di-t-butyldicarbonate in acetonitrile at room temperature, followed by stirring 20 minutes. After 220 mg (1.0 mmol) of 2-allylamino-4-amino-7-methylthieno[3,2-d]pyrimidine was added to the reaction solution, the mixture was stirred at room temperature for 2 hours. Further, 142 mg (2.0 mmol) of pyrrolidine was added thereto, followed by heating under reflux for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by a silica gel chromatography (eluent: ethyl acetate-hexane=1/2] to give 181 mg (yield: 57.1%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. temperatureby heating
  3. temperatureunder reflux for 16 hours
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by a silica gel chromatography (eluent

Sources & evidence

ORD record
ord-c7d47e2eae714395abedeb59aefb5bf9
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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