Dichloromethane → HCID 118024039, compound

HRID 2171786Notes

Reaction equation

HRID 2171786 reaction equation
[CH:1]1([C:7]2[S:18][C:10]3[N:11]=[C:12]([CH3:17])[N:13]=[C:14]([CH2:15]O)[C:9]=3[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)[Cl:20].S(Cl)(Cl)=O>CN(C=O)C>[Cl:20][CH2:15][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:18][C:10]=2[N:11]=[C:12]([CH3:17])[N:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 118023920HCID 118023920, compound

Product 1

HCID 118024039HCID 118024039, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (6-cyclohexyl-2-methylthieno[2,3-d]pyrimidin-4-yl)methanol (1.28 g) and DCM (20 mL) were added thionyl chloride (1 mL) and DMF (50 μL), followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, azeotroped with toluene, and dried. To the residue was added EtOAc. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The residue was purified by silica gel column (chloroform/EtOAc) to obtain 4-(chloromethyl)-6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine (663 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customazeotroped with toluene
  3. customdried
  4. additionTo the residue was added EtOAc
  5. washThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column (chloroform/EtOAc)

Sources & evidence

ORD record
ord-24b512b024754b0ca66111ab82b4ae58
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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