tert-butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate → 2-((1R,2S)-2-Aminocyclohexylamino)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one

HRID 515955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515955
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[C:13]2[C:12]([NH:16][C:17]3[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)=[N:11][C:10]([NH:24][C@@H:25]3[CH2:30][CH2:29][CH2:28][CH2:27][C@@H:26]3[NH:31]C(=O)OC(C)(C)C)=[N:9][C:8]=2[CH2:7]1>C(O)(C(F)(F)F)=O>[NH2:31][C@H:26]1[CH2:27][CH2:28][CH2:29][CH2:30][C@H:25]1[NH:24][C:10]1[N:11]=[C:12]([NH:16][C:17]2[CH:18]=[C:19]([CH3:23])[CH:20]=[CH:21][CH:22]=2)[C:13]2[C:14](=[O:15])[NH:6][CH2:7][C:8]=2[N:9]=1

Komponenten

3

Edukt 1

HCID 86654702tert-butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate

Produkt 1

HCID 532517972-((1R,2S)-2-Aminocyclohexylamino)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of crude tert-butyl (1S,2R)-2-(6-(2,4-dimethoxybenzyl)-5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate (235 mg, 0.390 mmol) in TFA (5 mL) was stirred at 60° C. for 2 h and was then purified by reverse phase preparative HPLC. The fractions were collected, concentrated under reduced pressure, diluted in EtOAc, and basified with an aqueous saturated solution of NaHCO3. The organic extract was dried and concentrated under reduced pressure to give the title compound as a white solid (60 mg, 44%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33-1.60 (m, 10 H), 2.32 (s, 3 H), 3.16 (m, 2 H), 3.92 (br s, 1 H), 4.14 (s, 2 H), 6.88 (d, J=7.07 Hz, 1 H), 7.13 (br s, 1 H), 7.22 (t, J=7.45 Hz, 1 H), 7.34-7.55 (m, 1 H), 7.70 (br s, 1 H), 8.01 (br s, 1 H), 8.58 (br s, 1 H). [M+H] calc'd for C19H24N6O, 353; found, 353.

Aufarbeitung

  1. customwas then purified by reverse phase preparative HPLC
  2. customThe fractions were collected
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted in EtOAc
  5. extractionThe organic extract
  6. customwas dried
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d2326f9343dd4cb7bd6905356ed4c20d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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