Cyclohexylamine → HCID 18326406, compound

HRID 1250661Notes

Reaction equation

HRID 1250661 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].[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(#N)C>[CH2:16]([NH:19][C:20]1[N:21]=[C:22]([NH:30][C:1](=[O:5])[NH:37][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:23]2[S:28][CH:27]=[C:26]([CH3:29])[C:24]=2[N:25]=1)[CH:17]=[CH2:18]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 90495Di-tert-butyl dicarbonateHCID 18326385HCID 18326385, compound

Product 1

HCID 18326406HCID 18326406, compoundYield 49.9%

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, 139 mg (1.4 mmol) of cyclohexylamine 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=1/4) to give 172 mg (yield: 49.9%) 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: ethyl acetate-hexane=1/4)

Sources & evidence

ORD record
ord-d89d6565adf04903b5333dd30add7882
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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