Ethanol → HCID 178470710, compound

HRID 2268823Notes

Reaction equation

HRID 2268823 reaction equation
[CH3:1][C:2]1[C:23]([CH3:24])=[CH:22][C:5]2[N:6]=[C:7]([NH:9][C:10]3[N:15]=[C:14]([OH:16])[C:13]([CH2:17][C:18]([OH:20])=[O:19])=[C:12]([CH3:21])[N:11]=3)[NH:8][C:4]=2[CH:3]=1.[CH2:25](O)[CH3:26]>OS(O)(=O)=O>[CH3:1][C:2]1[C:23]([CH3:24])=[CH:22][C:5]2[N:6]=[C:7]([NH:9][C:10]3[N:15]=[C:14]([OH:16])[C:13]([CH2:17][C:18]([O:20][CH2:25][CH3:26])=[O:19])=[C:12]([CH3:21])[N:11]=3)[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 178422319HCID 178422319, compound

Product 1

HCID 178470710HCID 178470710, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of (2) (0.935 g, 2.86 mmol) in ethanol (20 mL) and concentrated H2SO4 (3.5 mL) was heated at reflux for 24 h. The ethanol was evaporated in vacuo, cold water (30 mL) was added and the solution was then neutralised with NaOH 10M. The mixture was extracted with CHCl3 (4×20 ml,) and the combined organic phases were dried (MgSO4) and evaporated in vacuo. The resulting residue was triturated with ethanol and filtered to give 0.190 g (19%) of 2-[(5,6-Dimetlhyl-2-benzoimidazolyl)amino]-4-hydroxy-6-methyl-5-pyrimidine acetic acid, ethyl ester (1). mp: >300° C. (CF3CO2H/C2H5OH). IR (KBr): υ=3254, 2968, 2922, 1737, 1623, 1560, 1344, 1294, 774 cm−1. Accurate mass: calculated: 355.1644. Found 327.1644. Analysis calculated for C18H21N5O3: C, 60.83; H, 5.96; N, 19.71. Found: C, 60.1; H, 5.7; N, 18.7.

Workup

  1. temperatureat reflux for 24 h
  2. customThe ethanol was evaporated in vacuo, cold water (30 mL)
  3. additionwas added
  4. extractionThe mixture was extracted with CHCl3 (4×20 ml,)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe resulting residue was triturated with ethanol
  8. filtrationfiltered

Sources & evidence

ORD record
ord-7ad99678741f4cf3b97d14e9dbb35a49
Source dataset
uspto-grants-2001_12
Patent number
US06329383B1

Reaction notes

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