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

HRID 516012Notes

Reaction equation

HRID 516012 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dd596e4ccf2c491397d9f6ae21ff14af
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

Loading…