Hydrochloric Acid → Ethyl 2-[6-(aminomethyl)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxylate

HRID 2079810Notes

Reaction equation

HRID 2079810 reaction equation
C(OC([NH:8][CH2:9][CH:10]1[CH:15]2[CH:11]1[CH2:12][N:13]([C:16]1[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1)[CH2:14]2)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[NH2:8][CH2:9][CH:10]1[CH:15]2[CH:11]1[CH2:12][N:13]([C:16]1[N:17]=[CH:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][N:21]=1)[CH2:14]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 49857515Ethyl 2-(6-{[(tert-butoxycarbonyl)amino]methyl}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate

Product 1

HCID 49857516Ethyl 2-[6-(aminomethyl)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxylateYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 2-(6-{[(tert-butoxycarbonyl)amino]methyl}-3-azabicyclo[3.1.0]hex-3-yl)pyrimidine-5-carboxylate (1.7 g, 4.7 mmol) was stirred in DCM (20 ml) at r.t. under N2. 4M HCl in dioxane (2.35 ml, 9.4 mmol) was added, immediately causing a solid to precipitate. The reaction was left to stir for 30 min and then the solvent was removed in vacuo. The residue was dissolved in DCM (100 ml) and washed with sat. aq. NaHCO3 (100 ml). The organic layer was then dried (Na2SO4) and the solvent removed in vacuo to give the title compound as an orange solid (1.2 g, 97%). LCMS purity 97%, m/z 263 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 0.64 (1H, m), 1.29 (3H, t, J=7.2 Hz), 1.58 (2H, m), 3.33 (4H, m), 3.55 (2H, d, J=11.7 Hz), 3.82 (2H, d, J=11.7 Hz), 4.26 (2H, q, J=7.2 Hz), 8.76 (2H, s).

Workup

  1. customto precipitate
  2. waitThe reaction was left
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in DCM (100 ml)
  5. washwashed with sat. aq. NaHCO3 (100 ml)
  6. dry with materialThe organic layer was then dried (Na2SO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c5adadff237a48a8bede56d61d60af99
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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