Guanidine Hydrochloride → HCID 178431786, compound

HRID 28565

Reaction equation

HRID 28565 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[CH3:6][CH:7]([C:13](OCC)=[O:14])[C:8](OCC)=[O:9].C[O-].[Na+]>C(O)C>[NH2:4][C:3]1[N:5]=[C:8]([OH:9])[C:7]([CH3:6])=[C:13]([OH:14])[N:2]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 11857Diethyl methylmalonateHCID 10942334Sodium Methoxide

Product 1

HCID 178431786HCID 178431786, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred mixture of guanidine hydrochloride (1.91 g, 20.0 mmol) and diethyl methylmalonate (3.48 g, 20.0 mmol) in ethanol (30 ml) was added sodium methoxide (2.7 g, 50.0 mmol, 25% in methanol) dropwise. The cloudy mixture was stirred at 60-70° C. for 16 hours. After evaporation of volatiles under reduced pressure, the residue was treated with 1.0 M hydrochloric acid until pH=2. Filtration and drying provided 2-amino-4,6-dihydroxy-5-methyl-pyrimidine (2.5 g, 90% yield) as a white powder.

Workup

  1. customAfter evaporation of volatiles under reduced pressure
  2. additionthe residue was treated with 1.0 M hydrochloric acid until pH=2
  3. filtrationFiltration
  4. customdrying

Sources & evidence

ORD record
ord-1761c4aa3b9744399647612277241c1c
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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