Sodium ethoxide → HCID 178435045, compound

HRID 625030Notes

Reaction equation

HRID 625030 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].CC[O-].[Na+].[CH3:9][CH:10]1[CH:14]([C:15](OC)=[O:16])[C:13](=O)[CH2:12][S:11]1>C(O)C>[CH3:9][CH:10]1[C:14]2[C:15]([OH:16])=[N:4][CH:2]=[N:3][C:13]=2[CH2:12][S:11]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 12710774HCID 12710774, compound

Product 1

HCID 178435045HCID 178435045, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of formamidine HCl salt (37.3 g, 463 mmol) in ethanol (300 mL) was slowly added NaOEt (21%, 169 mL, 453 mmol). The mixture was stirred at room temperature for 1 hour and then filtered. To the filtrate was added methyl 2-methyl-4-oxo-tetrahydrothiophene-3-carboxylate (79 g, 453 mmol). The mixture was stirred at room temperature for 1 hour and then refluxed overnight. After cooling, the solvent was removed and the residue was purified by silica gel chromatography, eluted with Hexane/ethyl acetate (2:1-0:1)-DCM/MeOH (20:1) to afford 5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-ol (36 g, 47%). 1H NMR (CDCl3, 400 MHz) δ 12.83 (s, 1H), 4.68 (m, 1H), 4.32-4.08 (m, 2H), 1.66 (m, 3H). MS (APCI+) [M+H]+ 169.

Workup

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. temperaturerefluxed overnight
  4. temperatureAfter cooling
  5. customthe solvent was removed
  6. customthe residue was purified by silica gel chromatography
  7. washeluted with Hexane/ethyl acetate (2:1-0:1)-DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-43d66db2465948b4a659c8dd4455b70c
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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