Hydrochloric Acid → tert-Butyl (1-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)piperidin-2-yl)methylcarbamate

HRID 711476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711476
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:16]1[N:21]=[C:20]([C:22]#[N:23])[C:19]([C:24](OC)=[O:25])=[C:18]([NH:28][C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>[Pd].CCO>[O:25]=[C:24]1[C:19]2[C:18]([NH:28][C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)=[N:17][C:16]([N:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]3[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:21][C:20]=2[CH2:22][NH:23]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 67238205Methyl 2-(2-((tert-butoxycarbonylamino)methyl)piperidin-1-yl)-4-cyano-6-(m-tolylamino)pyrimidine-5-carboxylate

Produkt 1

HCID 86654716tert-Butyl (1-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)piperidin-2-yl)methylcarbamateAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(2-((tert-butoxycarbonylamino)methyl)piperidin-1-yl)-4-cyano-6-(m-tolylamino)pyrimidine-5-carboxylate (310.1 mg, 0.645 mmol), palladium on carbon (72.4 mg, 0.680 mmol) in EtOH (8 mL), and 1N HCl (4 mL) was stirred at RT for 16 h. The mixture was filtered to remove the catalyst. The filtrate was treated with saturated aq NaHCO3 (20 mL) for 3 h. The mixture was concentrated under reduced pressure and the residue was extracted with EtOAc (2×40 mL). The organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL), and brine (20 mL), were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (213.4 mg, 73%). 1H-NMR (DMSO-d6) δ ppm 1.28 (s, 9H), 1.35 (br s, 1H), 1.49-1.56 (m, 2H), 1.67-1.69 (m, 3H), 2.31 (s, 3H), 3.06 (br s, 1H), 3.24 (br s, 2H), 4.16 (s, 2H), 4.67 (br s, 1H), 5.08 (br s, 1H), 6.77 (br s, 1H), 6.87 (d, 1H, J=7.0 Hz), 7.23-7.25 (m, 1H), 7.53 (br s, 2 h), 8.07 (s, 1H), 8.55 (s, 1H). [M+H] calc'd for C24H33N6O3, 453. found, 453.5.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. additionThe filtrate was treated with saturated aq NaHCO3 (20 mL) for 3 h
  4. concentrationThe mixture was concentrated under reduced pressure
  5. extractionthe residue was extracted with EtOAc (2×40 mL)
  6. washThe organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL), and brine (20 mL)
  7. dry with materialwere dried over anhydrous Na2SO4
  8. filtrationfiltered through SiO2
  9. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b895ffb2099c4984a3a20cb01ed3ea86
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181255B2

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