Hydrochloric Acid → HCID 178517404, compound

HRID 1984307Notes

Reaction equation

HRID 1984307 reaction equation
[Na].Cl.[CH:3]1([C:6](=[NH:8])[NH2:7])[CH2:5][CH2:4]1.C([O:11][C:12](=O)[CH:13]([F:19])[C:14](OCC)=[O:15])C.Cl>CO.O>[CH:3]1([C:6]2[N:7]=[C:14]([OH:15])[C:13]([F:19])=[C:12]([OH:11])[N:8]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12702Diethyl fluoromalonateHCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 5360545Sodium2×

Product 1

HCID 178517404HCID 178517404, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium (646 mg, 28 mmol) is dissolved in methanol (50 ml) under a nitrogen atmosphere. Cyclopropanecarboximidamide hydrochloride (3.40 g, 28 mmol) is added in one portion. The mixture is stirred at room temperature for 0.25 h, then filtered upon hyflocel. The filtrate is concentrated in vacuo. This free base is added to a solution of sodium (1.29 g, 56 mmol) in methanol (50 ml) under a nitrogen atmosphere, at room temperature. Diethylfluoromalonate (5 g, 28 mmol) is added and the mixture is stirred at 60° C. for 5 h. The solvent is evaporated and the yellowish solid obtained is dissolved in 60 ml of water. The pH is adjusted at 6 with a 5 N HCl solution and the white precipitate formed is filtered and dried. 2-cyclopropyl-5-fluoro-4,6-pyrimidinediol 3 (3.6 g, 76%) is obtained as a white powder and used in the next step without further purification.

Workup

  1. filtrationfiltered upon hyflocel
  2. concentrationThe filtrate is concentrated in vacuo
  3. stirringthe mixture is stirred at 60° C. for 5 h
  4. customThe solvent is evaporated
  5. customthe yellowish solid obtained
  6. customthe white precipitate formed
  7. filtrationis filtered
  8. customdried

Sources & evidence

ORD record
ord-bf5c01449e5d4e2684797d67c6268998
Source dataset
uspto-grants-2009_06
Patent number
US07544675B2

Reaction notes

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