Trifluoroacetic acid → 3-Methoxy-5-(6-(piperidin-4-ylmethylamino)pyrimidin-4-ylamino)-pyrazine-2-carbonitrile

HRID 556884Notes

Reaction equation

HRID 556884 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:10]1[N:11]=[CH:12][C:13]([NH:18][C:19]2[N:24]=[CH:23][N:22]=[C:21]([NH:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)[CH:20]=2)=[N:14][C:15]=1[O:16][CH3:17])#[N:9]>ClCCl>[CH3:17][O:16][C:15]1[C:10]([C:8]#[N:9])=[N:11][CH:12]=[C:13]([NH:18][C:19]2[CH:20]=[C:21]([NH:25][CH2:26][CH:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[N:22]=[CH:23][N:24]=2)[N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59613473tert-Butyl 4-((6-(5-cyano-6-methoxypyrazin-2-ylamino)pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 596134993-Methoxy-5-(6-(piperidin-4-ylmethylamino)pyrimidin-4-ylamino)-pyrazine-2-carbonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL) was added to a solution of tert-butyl 4-((6-(5-cyano-6-methoxypyrazin-2-ylamino)-pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate (3 mg, 0.0068 mmol) in dichloromethane (3 mL) at room temperature. After 2 hr, the solution was evaporated to dryness and purified by ion exchange on SCX-II acidic resin (500 mg), eluting with methanol then 2M ammonia-methanol. The basic fractions were combined and the solvent was removed in vacuo to give the title compound as yellow oil (1.5 mg, 65%).

Workup

  1. customthe solution was evaporated to dryness
  2. custompurified by ion exchange on SCX-II acidic resin (500 mg)
  3. washeluting with methanol
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6738f92e11bf4b158c9dd4051df7dab6
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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