Ethanol → HCID 178433477, compound

HRID 1663460Notes

Reaction equation

HRID 1663460 reaction equation
[Na].CCO.[F:5][CH:6]([C:12]([O:14]CC)=O)[C:7]([O:9]CC)=O.Cl.[C:18]([NH2:21])(=[NH:20])[CH3:19]>>[OH:9][C:7]1[C:6]([F:5])=[C:12]([OH:14])[N:21]=[C:18]([CH3:19])[N:20]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 12702Diethyl fluoromalonateHCID 67170Acetamidine monohydrochlorideHCID 5360545Sodium2×

Product 1

HCID 178433477HCID 178433477, compoundYield 64.4%

Procedure

Part A: A mixture of sodium metal (1.55 g, 67.4 mmol) and EtOH (15.0 mL, 257 mmol) was stirred at RT until nearly all sodium had reacted. Diethyl fluoromalonate (3.54 mL, 22.4 mmol) was added followed by acetamidine hydrochloride (2.14 g, 22.7 mmol). The reaction mixture was heated at reflux for 3 h, cooled to RT and concentrated under reduced pressure. The residue was diluted with water (ca. 50 mL) and acidified (pH=2) with 6M aqueous HCl, and the mixture was stirred at RT for 1 h as a precipitate formed. The solids were collected by suction filtration and washed with water. Excess solvent was removed in vacuo to give 4,6-dihydroxy-5-fluoro-2-methylpyrimidine (2.08 g, 64%) as a light gray solid. LCMS (m/z): 145 (M+H)+

Workup

  1. customhad reacted
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 3 h
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with water (ca. 50 mL)
  6. customformed
  7. filtrationThe solids were collected by suction filtration
  8. washwashed with water
  9. customExcess solvent was removed in vacuo

Sources & evidence

ORD record
ord-319e066a0a13411fb57c28ee6cab2708
Source dataset
uspto-grants-2011_10
Patent number
US08034954B2

Reaction notes

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