Toluene → HCID 118023129, compound

HRID 2171773Notes

Reaction equation

HRID 2171773 reaction equation
[CH:1]1([C:7]2[S:17][C:10]3[N:11]=[C:12]([CH3:16])[NH:13][C:14](=O)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O>CN(C=O)C>[Cl:27][C:14]1[C:9]2[CH:8]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[S:17][C:10]=2[N:11]=[C:12]([CH3:16])[N:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 118023539HCID 118023539, compound

Product 1

HCID 118023129HCID 118023129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4(3H)-one (25.0 g) and toluene (300 mL) were added phosphorous oxychloride (14 mL) and DMF (200 μL), followed by heating to reflux at 150° C. for 14 hours. The reaction mixture was left to be cooled to room temperature and concentrated under reduced pressure. To the residue were added chloroform, water, and saturated aqueous sodium bicarbonate, followed by stirring. The reaction mixture was extracted with chloroform. The organic layer was washed sequentially with water and brine. To the organic layer were added MgSO4, activated carbon (2 g), and silica gel (100 mL), followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain 4-chloro-6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine (27.4 g).

Workup

  1. temperatureby heating
  2. waitThe reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue were added chloroform, water, and saturated aqueous sodium bicarbonate
  6. extractionThe reaction mixture was extracted with chloroform
  7. washThe organic layer was washed sequentially with water and brine
  8. additionTo the organic layer were added MgSO4, activated carbon (2 g), and silica gel (100 mL)
  9. stirringby stirring
  10. filtrationThe mixture was filtered through Celite
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ef3f9c984f447f48c4dd01f672593d0
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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