Ethanol → HCID 178516643, compound

HRID 1920829Notes

Reaction equation

HRID 1920829 reaction equation
[H-].[Na+].C(O)C.[C:6](OCC)(=[O:13])[CH2:7][C:8](OCC)=[O:9].Cl.[O:18]1[CH2:23][CH2:22][CH:21]([C:24](=[NH:26])[NH2:25])[CH2:20][CH2:19]1>CCCCCC>[O:18]1[CH2:23][CH2:22][CH:21]([C:24]2[N:25]=[C:8]([OH:9])[CH:7]=[C:6]([OH:13])[N:26]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 43811032Oxane-4-carboximidamide--hydrogen chloride (1/1)

Product 1

HCID 178516643HCID 178516643, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of sodium hydride (3.0 g, 60% in oil, 75 mmol) in hexane (4 mL) was added ethanol (60 mL) slowly at rt. After 30 min at rt, diethyl malonate (4 g, 25 mmol) were added, followed by tetrahydro-2H-pyran-4-carboximidamide-HCl (4.12 g, 25 mmol). The mixture was heated at 90° C. overnight. Dry molecular sieves (2.5 g) were added, and additional ethanol was added to help stirring. The reaction was heated at 90° C. for 4 days. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was removed in vacuo to give 2-(tetrahydro-2H-pyran-4-yl)pyrimidine-4,6-diol as a solid, which was used for next step without further purification.

Workup

  1. customDry molecular sieves (2.5 g)
  2. additionwere added
  3. additionadditional ethanol was added
  4. temperatureThe reaction was heated at 90° C. for 4 days
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationfiltered through Celite
  7. customThe filtrate was removed in vacuo

Sources & evidence

ORD record
ord-6a8816800822428eb3d513bce7af4253
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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