Tert-Butylamine → HCID 18326431, compound

HRID 1250659Notes

Reaction equation

HRID 1250659 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].[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32].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][C:31]([CH3:34])([CH3:33])[CH3:32])[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 6385Tert-ButylamineHCID 90495Di-tert-butyl dicarbonateHCID 18326385HCID 18326385, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18326431HCID 18326431, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 306 mg (1.4 mmol) of di-t-butyldicarbonate in acetonitrile was added 122 mg (1.0 mmol) of N,N-dimethylaminopiridine at room temperature, followed by stirring for 20 minutes. 220 mg (1.0 mmol) of 2-allylamino-4-amino-7-methylthieno[3,2-d]pyrimidine was added to the reaction solution, followed by stirring at room temperature for 2 hours. Further, after 102 mg (1.4 mmol) of t-butylamine was added to the mixture, the reaction mixture was subjected to 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=1/23 to give 161 mg (yield: 50.5%) of the title compound.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. temperatureto 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-2f5109559acd4505806b88bd653f24e2
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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