1,3-Propanediol → HCID 54145203, compound

HRID 544573Notes

Reaction equation

HRID 544573 reaction equation
[CH2:1]([N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1)[CH2:2][CH3:3].[H-].[Na+].[CH2:19]([OH:23])[CH2:20][CH2:21][OH:22]>O>[CH2:1]([N:4]=[C:5]([NH2:16])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([O:22][CH2:21][CH2:20][CH2:19][OH:23])[N:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 54392836HCID 54392836, compound

Product 1

HCID 54145203HCID 54145203, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-Propylguanidino)-2-methylsulphinylpyrimidine (200 mg.) was added to a solution of sodium hydride (72 mg.) in 1,3-propanediol (2 ml.) and the mixture stirred at ambient temperature for 1 hour. The mixture was diluted with water and extracted with EtOAc (3×10 ml.). The extract was dried (MgSO4) and evaporated to give a gum which crystallised on standing. Recrystallisation from EtOAc gave 4-(2-propylguanidino)-2-(3-hydroxypropoxy)pyrimidine, m.p. 183°-184° (yield 25%).

Workup

  1. extractionextracted with EtOAc (3×10 ml.)
  2. dry with materialThe extract was dried (MgSO4)
  3. customevaporated
  4. customto give a gum which
  5. customcrystallised
  6. customRecrystallisation from EtOAc

Sources & evidence

ORD record
ord-5350576557a1407db5a8c6c3738ff2e7
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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