Allylamine → HCID 18326537, compound

HRID 1250662Notes

Reaction equation

HRID 1250662 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].[CH2:31]([NH2:34])[CH:32]=[CH2:33].C(OCC)(=O)C.CCCCCC>C(#N)C>[CH2:16]([NH:19][C:20]1[N:21]=[C:22]([NH:30][C:1](=[O:5])[NH:34][CH2:31][CH:32]=[CH2:33])[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 7853AllylamineHCID 90495Di-tert-butyl dicarbonateHCID 18326385HCID 18326385, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18326537HCID 18326537, compoundYield 18.8%

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, 80 mg (1.4 mmol) of allylamine 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 54 mg (yield: 18.8%) 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-0cf5fb92d0b540a6b56f5d3c1d2f8b4d
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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