Guanidine Hydrochloride → HCID 178439780, compound

HRID 1752153Notes

Reaction equation

HRID 1752153 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CC[O-].[Na+].[CH2:10]([CH:13]([C:19](OCC)=[O:20])[C:14](OCC)=[O:15])[CH:11]=[CH2:12]>CCO>[CH2:10]([C:13]1[C:19]([OH:20])=[N:4][C:3]([NH2:5])=[N:2][C:14]=1[OH:15])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 74900Diethyl allylmalonateHCID 2723922Sodium ethoxide

Product 1

HCID 178439780HCID 178439780, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Guanidine hydrochloride (27 g, 0.28 mol) was added to cold absolute EtOH (200 mL) and NaOEt (30% in ethanol) (200 mL), and the mixture was stirred at 0° C. for 10 min. After this time, diethyl allylmalonate (55 g, 0.28 mol) was added. The reaction mixture was then stirred at room temperature for 18 h. Acidification with 3N HCl precipitated the crude product (pH=6). The solid was collected by filtration and washed with ethanol. Recrystallization from water afforded 29 g (62%) of pure 5-allyl-2-amino-4,6-dihydroxypyrimidine (CXLIII). LCMS (ESI) m/z=168 (M+H)+.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 18 h
  2. customAcidification with 3N HCl precipitated the crude product (pH=6)
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethanol
  5. customRecrystallization from water

Sources & evidence

ORD record
ord-380c0bd11fc34659b9affe905b214c08
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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