Guanidine Hydrochloride → 2-Aminopyrimidine-5-carbaldehyde

HRID 509951Notes

Reaction equation

HRID 509951 reaction equation
C[NH+]([CH2:4][C:5]([CH2:10]N(C)C)=[CH:6][NH+](C)C)C.Cl.[NH2:15][C:16]([NH2:18])=[NH:17].[OH-:19].[Na+]>C(#N)C.O>[NH2:17][C:16]1[N:18]=[CH:6][C:5]([CH:10]=[O:19])=[CH:4][N:15]=1

Participants

6

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 101612644Vinamidinium

Product 1

HCID 7690972-Aminopyrimidine-5-carbaldehydeYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Vinamidinium salt (68, 158 g, 413 mmol) and guanidine hydrochloride (69, 63.3 g, 455 mmol) were dissolved in 527 mL of acetonitrile and cooled on an ice/water bath. Sodium hydroxide (66.1 mL, 50% w/w, 827 mmol) was added dropwise, keeping the temperature below 25° C. The reaction was allowed to warm to 25° C. and stirred for 4 hours, then diluted with water and filtered, stripped from ethanol/heptane, then triturated with heptane. The resulting solid was dried under vacuum to provide the desired compound (70, 37 g, 301 mmol, 72.7% yield).

Workup

  1. temperaturecooled on an ice/water bath
  2. customthe temperature below 25° C
  3. filtrationfiltered
  4. customtriturated with heptane
  5. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-39a7bd8d7676421aba74e057bdfad832
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

Loading…