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

HRID 588709Notes

Reaction equation

HRID 588709 reaction equation
[NH2:1][C:2](=[NH:15])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O=[C:17]1[CH2:22][CH2:21][O:20][CH2:19][CH:18]1[C:23](OC)=[O:24].C(=O)([O-])[O-].[K+].[K+]>CO>[O:24]=[C:23]1[NH:1][C:2]([CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:15][C:17]2[CH2:22][CH2:21][O:20][CH2:19][C:18]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 244144Benzyl 2-amino-2-iminoethylcarbamateHCID 14666555Methyl 4-oxooxane-3-carboxylate

Product 1

HCID 135741884Benzyl ((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-D]pyrimidin-2-YL)methyl)carbamateYield 60.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To benzyl 2-amino-2-iminoethylcarbamate (1.77 g, 8.54 mmol) in methanol (67.5 mL) was added methyl 4-oxotetrahydro-2H-pyran-3-carboxylate (1.35 g, 8.54 mmol) and potassium carbonate (3.54 g, 25.6 mmol). The reaction mixture was stirred 15 h at room temperature. The solution was filtered and concentrated under vacuum. Purification was accomplished on a 100 g Isco column with 0% to 10% methanol in dichloromethane over 20 column volumes to give title compound (1.63 g, 59% yield). Exact mass calculated for C16H17N3O4 315.3. found 316.2 (ESI, M+H); 1H NMR (400 MHz, MeOD) δ ppm 7.17-7.46 (m, 5H) 5.11 (s, 2H) 4.47 (br. s., 2H) 4.22 (s, 2H) 3.92 (t, J=5.31 Hz, 2H) 2.65 (br. s., 2H).

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated under vacuum
  3. customPurification

Sources & evidence

ORD record
ord-50ae2f9734364890a773be49e7b08350
Source dataset
uspto-grants-2016_01
Patent number
US09227982B2

Reaction notes

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