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

HRID 516012ノート

反応式

HRID 516012 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]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]3[CH2:25][NH:26]C(=O)OC(C)(C)C)=[N:6][C:5]=2[CH2:4][NH:3]1.Cl>CC(O)=O>[NH2:26][CH2:25][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][N:19]1[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 86654716tert-Butyl (1-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)piperidin-2-yl)methylcarbamate

生成物 1

HCID 532524372-(2-(Aminomethyl)piperidin-1-yl)-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one収率 17%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of tert-butyl (1-(5-oxo-4-(m-tolylamino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)piperidin-2-yl)methylcarbamate (207.1 mg, 0.458 mmol) in HOAc (3 mL) was added HCl (1 mL, 32.9 mmol). The mixture was stirred at RT for 1 h and then concentrated under reduced pressure. The residue was treated with saturated aq NaHCO3 (50 mL) and was extracted with EtOAc-THF (1/1, 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. The filtrate was concentrated under reduced pressure and the residue was washed with EtOH to give the title compound as a pale yellow solid (27.4 mg, 17%). 1H-NMR (DMSO-d6) δ ppm 1.32-1.70 (m, 7H), 1.89-1.92 (m, 1H), 2.31 (s, 3H), 2.74-2.87 (m, 1H), 2.81-2.85 (m, 1H), 2.94 (br s, 1H), 4.17 (s, 2H), 4.68-4.79 (m, 2H), 6.88 (d, 1H, J=7.5 Hz), 7.22-7.25 (m, 1H), 7.49-7.50 (m, 1H), 7.60 (s, 1H), 8.06 (s, 1H), 8.58 (s, 1H). [M+H] calc'd for C19H25N6O, 353; found, 353.5.

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with saturated aq NaHCO3 (50 mL)
  3. extractionwas extracted with EtOAc-THF (1/1, 2×40 mL)
  4. washThe organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL), and brine (20 mL)
  5. dry with materialwere dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe residue was washed with EtOH

出典と根拠

ORDレコード
ord-dd596e4ccf2c491397d9f6ae21ff14af
出典データセット
uspto-grants-2015_08
特許番号
US09108970B2

反応ノート

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