Sodium ethoxide → Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamate

HRID 713381Notes

Reaction equation

HRID 713381 reaction equation
O=[C:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10]C)=O.Cl.[NH2:13][C:14](=[NH:27])[CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[O-]CC.[Na+]>C(O)C>[O:10]=[C:8]1[NH:27][C:14]([CH2:15][NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:13][C:2]2[CH2:7][CH2:6][O:5][CH2:4][C:3]1=2

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 14666555Methyl 4-oxooxane-3-carboxylateHCID 18943499Benzyl (2-amino-2-iminoethyl)carbamate hydrochloride

Product 1

HCID 135741884Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamateYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-oxotetrahydro-2H-pyran-3-carboxylate (51.1 g, 323 mmol) and benzyl 2-amino-2-iminoethylcarbamate hydrochloride (78.8 g, 323 mmol) in anhydrous ethanol was added sodium ethoxide (122 mL, 323 mmol, 21% in ethanol). The mixture was mechanically stirred, heated at reflux for 24 h, cooled down to ambient temperature, and filtered to give the title compound (55.6 g, 55% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.40 (br. s., 1H), 7.69 (t, J=5.8 Hz, 1H), 7.15-7.44 (m, 5H), 4.99-5.08 (m, 2H), 4.35 (s, 2H), 4.04-4.11 (m, 2H), 3.84 (t, J=5.3 Hz, 2H), 2.48-2.57 (m, 2H). MS m/z 316.2 (M+1), retention time=1.10 min.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bfd0f09876294c08b347d0ea6335f56d
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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