Thionyl Chloride → HCID 11243073, compound

HRID 1725575Notes

Reaction equation

HRID 1725575 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][C:12]=3[S:13][C:7]=2[N:6]=[CH:5]1.S(Cl)([Cl:21])=O>ClCCCl>[Cl:21][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][C:12]=3[S:13][C:7]=2[N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15453507HCID 15453507, compound

Product 1

HCID 11243073HCID 11243073, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

42.0 g (158 mM) of 3-(2-hydroxyethyl)-7-methyl-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one in 240 ml of 1,2-dichloroethane were heated to reflux and then 12.7 ml (175 mM) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After refluxing for 2 h, the reaction mixture was allowed to cool and was poured into ice/water. The mixture was partitioned between methylene chloride and water at pH=10, and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried and then concentrated. The crude product (40 g) was recrystallized from 400 ml of isopropanol. 30.5 g (68%) of product with melting point 159-161° C. were isolated.

Workup

  1. temperatureto reflux
  2. temperatureAfter refluxing for 2 h
  3. temperatureto cool
  4. customThe mixture was partitioned between methylene chloride and water at pH=10
  5. extractionthe aqueous phase was extracted with methylene chloride
  6. customThe combined organic phases were dried
  7. concentrationconcentrated
  8. customThe crude product (40 g) was recrystallized from 400 ml of isopropanol

Sources & evidence

ORD record
ord-214eba80acf643af93df7cc2faaad864
Source dataset
uspto-grants-2009_02
Patent number
US07491729B2

Reaction notes

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