Butylamine → HCID 18326482, compound

HRID 1250663Notes

Reaction equation

HRID 1250663 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]([NH2:35])[CH2:32][CH2:33][CH3:34].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:35][CH2:31][CH2:32][CH2:33][CH3:34])[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 8007ButylamineHCID 90495Di-tert-butyl dicarbonateHCID 18326385HCID 18326385, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18326482HCID 18326482, compoundYield 43.9%

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, 102 mg (1.4 mmol) of n-butylamine 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 140 mg (yield: 43.9%) 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-adb46d078529484fa067d1ed163459b5
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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