Triethylamine → tert-Butyl 4-((6-(5-cyano-6-methoxypyrazin-2-ylamino)pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384723
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:10]=[C:11]([O:17][CH3:18])[C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH:3]=1.[NH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C(N(CC)CC)C>C(#N)C>[C:15]([C:12]1[N:13]=[CH:14][C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)[CH:3]=2)=[N:10][C:11]=1[O:17][CH3:18])#[N:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 596135175-(6-Chloropyrimidin-4-ylamino)-3-methoxypyrazine-2-carbonitrile

Produkt 1

HCID 59613473tert-Butyl 4-((6-(5-cyano-6-methoxypyrazin-2-ylamino)pyrimidin-4-ylamino)methyl)piperidine-1-carboxylateAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 5-(6-chloropyrimidin-4-ylamino)-3-methoxypyrazine-2-carbonitrile (4.5 mg, 0.017 mmol), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (4 mg, 0.034 mmol) and triethylamine (12 uL, 0.085 mmol) in acetonitrile (1.5 mL) was heated at 145° C. for 90 min using microwave irradiation. The solvent was removed in vacuo and the crude mixture was purified by preparative thin layer chromatography, eluting with dichloromethane/MeOH (10/1), to give the title compound as a yellow oil (3 mg, 40%).

Aufarbeitung

  1. custommicrowave irradiation
  2. customThe solvent was removed in vacuo
  3. customthe crude mixture was purified by preparative thin layer chromatography
  4. washeluting with dichloromethane/MeOH (10/1)

Quellen und Nachweise

ORD-Eintrag
ord-1d2eebfb2a714ea885b557fbc721b2cf
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367658B2

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