Hydrogen chloride-ethyl acetate → HCID 118023489, compound

HRID 2171784Notes

Reaction equation

HRID 2171784 reaction equation
C([O:9][CH2:10][C:11]1[C:12]2[N:20]=[C:19]([CH:21]3[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]3)[S:18][C:13]=2[N:14]=[C:15]([CH3:17])[N:16]=1)(=O)C1C=CC=CC=1.O(C)[Na].Cl.CCOC(C)=O>CO>[CH3:27][C:24]1([CH3:28])[CH2:23][CH2:22][CH:21]([C:19]2[S:18][C:13]3[N:14]=[C:15]([CH3:17])[N:16]=[C:11]([CH2:10][OH:9])[C:12]=3[N:20]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 21866389Hydrogen chloride-ethyl acetateHCID 118024047HCID 118024047, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 118023489HCID 118023489, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixture of [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl benzoate (13.8 g) and MeOH (250 mL) was added a 28% NaOCH3 solution (670 μL) in MeOH, followed by stirring at room temperature for 3 hours. The reaction mixture was neutralized by the addition of 4 M HCl/EtOAc (870 μL), and concentrated under reduced pressure. To the residue was added water, followed by extraction with EtOAc. To the organic layer were added MgSO4 and basic silica gel, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methanol (7.9 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added water
  3. extractionfollowed by extraction with EtOAc
  4. additionTo the organic layer were added MgSO4 and basic silica gel
  5. stirringby stirring
  6. filtrationThe mixture was filtered through Celite
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-8ee72fba587b4eb4b3f88ecfab7e3069
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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