Hydrochloric Acid → 2-[(2-Methoxy-ethylamino)-methyl]-3,5,7,8tetrahydro-pyrano[4,3-d]pyrimidin-4-one

HRID 713468Notes

Reaction equation

HRID 713468 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:13][C:14]1[NH:15][C:16](=[O:24])[C:17]2[CH2:23][O:22][CH2:21][CH2:20][C:18]=2[N:19]=1)C(=O)OC(C)(C)C.Cl>O1CCOCC1>[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:13][C:14]1[NH:15][C:16](=[O:24])[C:17]2[CH2:23][O:22][CH2:21][CH2:20][C:18]=2[N:19]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136612914tert-butyl 2-methoxyethyl((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)carbamate

Product 1

HCID 1366272422-[(2-Methoxy-ethylamino)-methyl]-3,5,7,8tetrahydro-pyrano[4,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-methoxyethyl((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)carbamate (257 mg, 0.545 mmol) in dioxane (5 mL) was added hydrochloric acid (4M in dioxane, 0.818 mL, 3.3 mmol) and the solution was stirred for 8 h. The precipitate was filtered and washed with ether. The residue was re-dissolved in ether, and stirred overnight (8 h) in ether. The precipitate was filtered and washed with ether to yield the title compound as a hydrochloride salt (107 mg). 1H NMR (400 MHz, MeOD) δ ppm 4.50 (s, 2H) 4.27 (s, 2H) 3.90-4.03 (m, 3H) 3.66-3.77 (m, 2H) 3.43 (s, 3H) 3.35-3.41 (m, 3H) 2.74 (s, 2H). MS (m/z, MH+): 239.3

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether
  3. dissolutionThe residue was re-dissolved in ether
  4. stirringstirred overnight (8 h) in ether
  5. filtrationThe precipitate was filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-98509d0584d148dfbd93b1cfa452cc5a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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