Hydrochloric Acid → 2-((1R,2S)-2-Aminocyclohexylamino)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one

HRID 2092732ノート

反応式

HRID 2092732 の反応式
[O:1]=[C:2]1[C:10]2[C:9]([NH:11][C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[N:8][C:7]([NH:19][C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[NH:26]C(=O)OC(C)(C)C)=[N:6][C:5]=2[CH2:4][NH:3]1.Cl>CC(O)=O>[NH2:26][C@H:21]1[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]1[NH:19][C:7]1[N:8]=[C:9]([NH:11][C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)[C:10]2[C:2](=[O:1])[NH:3][CH2:4][C:5]=2[N:6]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86654703tert-Butyl (1S,2R)-2-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate

生成物 1

HCID 532517972-((1R,2S)-2-Aminocyclohexylamino)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one収率 29%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of tert-butyl (1S,2R)-2-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-ylamino)cyclohexylcarbamate (50.4 mg, 0.111 mmol) in HOAc (2 mL) was added hydrochloric acid (0.5 mL, 16.46 mmol). The mixture was stirred at RT for 30 min and then concentrated under reduced pressure. The residue was treated with saturated aq NaHCO3 and extracted with EtOAc. The organic layers were washed with saturated aq NaHCO3, water, and brine, were dried over anhydrous Na2SO4, and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, EtOAc/MeOH=20/1) to give the title compound as a white powder (11.3 mg, 29%). 1H NMR (400 MHz, CDCl3) δ ppm 1.48-1.80 (m, 10H), 2.37 (s, 3H), 3.24 (br s, 1H), 4.07 (br s, 1H), 4.20 (s, 2H), 5.55 (br s, 1H), 5.89 (br s, 1H), 6.89-6.91 (m, 1H), 7.22-7.24 (m, 1H), 7.53-7.63 (m, 2H), 8.49 (br s, 1H). [M+H] calc'd for C19H25N6O, 353. found, 353.

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with saturated aq NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with saturated aq NaHCO3, water, and brine
  5. dry with materialwere dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by column chromatography (SiO2, EtOAc/MeOH=20/1)

出典と根拠

ORDレコード
ord-f85ecfed5b514b06b861234c41244571
出典データセット
uspto-grants-2013_05
特許番号
US08440689B2

反応ノート

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