Ethanol → HCID 118023558, compound

HRID 2171777Notes

Reaction equation

HRID 2171777 reaction equation
[CH:1]1([C:7]2[S:18][C:10]3[N:11]=[C:12]([CH3:17])[N:13]=[C:14]([C:15]#N)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[O:20]1CCO[CH2:22][CH2:21]1.CC[OH:28]>>[CH:1]1([C:7]2[S:18][C:10]3[N:11]=[C:12]([CH3:17])[N:13]=[C:14]([C:15]([O:20][CH2:21][CH3:22])=[O:28])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 118023631HCID 118023631, compound

Product 1

HCID 118023558HCID 118023558, compound

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile (23.5 g) and EtOH (100 mL) was added 4 M HCl/dioxane (100 mL), followed by stirring at 80° C. for 2 days. The reaction mixture was left to be cooled to room temperature and concentrated under reduced pressure. To the residue was added chloroform, followed by dissolving therein, and activated carbon (2 g) and basic silica gel (100 mL) were further added thereto, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain ethyl 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine-4-carboxylate (30.8 g).

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added chloroform
  5. dissolutionby dissolving
  6. additionactivated carbon (2 g) and basic silica gel (100 mL) were further added
  7. stirringby stirring
  8. filtrationThe mixture was filtered through Celite
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-123fe932cfde4d4b947442ddd6271e71
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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