Hydrochloric Acid → HCID 178444387, compound

HRID 621396

Reaction equation

HRID 621396 reaction equation
Cl.[CH2:2]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([NH2:15])=[NH:14])[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][CH3:6].[CH3:16][O:17][CH:18]([C:23](OC)=[O:24])[C:19](OC)=[O:20].C[O-].[Na+].Cl>CO>[CH2:2]([C@H:7]1[CH2:8][CH2:9][C@H:10]([C:13]2[N:15]=[C:23]([OH:24])[C:18]([O:17][CH3:16])=[C:19]([OH:20])[N:14]=2)[CH2:11][CH2:12]1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78718Dimethyl methoxymalonateHCID 10942334Sodium MethoxideHCID 178444523HCID 178444523, compound

Product 1

HCID 178444387HCID 178444387, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This trans-4-pentylcyclohexanecarboxamidine hydrochloride (69 g, 0.30 mol) and dimethyl methoxymalonate (48 g, 0.30 mol) were added to a solution of sodium methylate (56 g, 1.0 mol) dissolved in anhydrous methanol (1 l), followed by heating the mixture under reflux with stirring for 5 hours, thereafter cooling the resulting material, mixing it with 6N-hydrochloric acid (500 ml), agitating the mixed liquid at room temperature for 20 minutes, filtering the liquid under suction through a filter, washing the resulting residue on the filter with water and methanol and drying it under reduced pressure to obtain 2-(trans-4-pentylcyclohexyl)-4,6-dihydroxy-5-methoxypyrimidine (67 g, 0.23 mol).

Workup

  1. temperatureby heating the mixture
  2. temperatureunder reflux
  3. temperaturecooling the resulting material
  4. stirringagitating the mixed liquid at room temperature for 20 minutes
  5. filtrationfiltering the liquid under suction through a filter
  6. washwashing the resulting residue on the
  7. filtrationfilter with water and methanol
  8. customdrying it under reduced pressure

Sources & evidence

ORD record
ord-75d317e262074094992716415ffca4bd
Source dataset
uspto-grants-1989_04
Patent number
US04824596

Linked notes

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