Methanimidamide, hydrochloride (1:1) → HCID 178499120, compound

HRID 1349466Notes

Reaction equation

HRID 1349466 reaction equation
[CH2:1]([O:8][C:9](=[C:19]([OH:21])C)[CH:10](C(OC)=O)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl.[CH:26]([NH2:28])=[NH:27]>CO>[CH2:1]([O:8][C:9]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[N:27][CH:26]=[N:28][C:19]=1[OH:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 69001488HCID 69001488, compound

Product 1

HCID 178499120HCID 178499120, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of dimethyl 2-benzyloxy-3-hydroxy-2-butenedicarboxylate (3.0 g) in methanol (60 ml) were added sodium methoxide (1.28 g) and formamidine hydrochloride (953 mg) under ice-cooling, and the mixture was stirred at 70° C. for 1.5 hr. The reaction solvent was evaporated under reduced pressure, and water was added to dissolve the residue. 5% Aqueous potassium hydrogen sulfate solution was added, and the precipitated solid was collected by filtration, washed with water and dried to give methyl 5-benzyloxy-6-hydroxypyrimidine-4-carboxylate (1.1 g).

Workup

  1. temperaturecooling
  2. customThe reaction solvent was evaporated under reduced pressure, and water
  3. additionwas added
  4. dissolutionto dissolve the residue
  5. addition5% Aqueous potassium hydrogen sulfate solution was added
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-31881679b2224afba9d0652e07c6cd69
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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