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Cyclopropanecarboximidamide hydrochloride → 2-Cyclopropylpyrimidin-4-ol

HRID 386109
Notes
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Reaction equation

HRID 386109 reaction equation
C(O[C:4](=[O:8])/[CH:5]=[CH:6]\[O-])C.[Na+].Cl.[CH:11]1([C:14](=[NH:16])[NH2:15])[CH2:13][CH2:12]1>O>[CH:11]1([C:14]2[N:16]=[C:4]([OH:8])[CH:5]=[CH:6][N:15]=2)[CH2:13][CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2781916Cyclopropanecarboximidamide hydrochlorideHCID 58190618sodium (Z)-3-ethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 1785164792-Cyclopropylpyrimidin-4-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium (1Z)-3-ethoxy-3-oxoprop-1-en-1-olate (6.60 g, 47.8 mmol) was dissolved in water (1.5 mL) and in a second flask cyclopropanecarboximidamide hydrochloride (3 g, 24.88 mmol) was dissolved in water (2 mL) and the contents of the second flask were added to the first flask. The reaction was allowed to stir for 72 hours. The reaction was then transferred to a separatory funnel and extracted with chloroform and a small amount of methanol. The water layer was extracted again and the combined organic layers were dried over magnesium sulfate, filtered and concentrated to a pale yellow solid. Diethyl ether was then added to precipitate product. The mixture was filtered and the solid was collected and dried to give the title compound.

Workup

  1. additionthe contents of the second flask were added to the first flask
  2. customThe reaction was then transferred to a separatory funnel
  3. extractionextracted with chloroform
  4. extractionThe water layer was extracted again
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a pale yellow solid
  8. additionDiethyl ether was then added
  9. customto precipitate product
  10. filtrationThe mixture was filtered
  11. customthe solid was collected
  12. customdried

Sources & evidence

ORD record
ord-708040ad3ea242c584d8d16a9ff0b2e5
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367706B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes