Dimethylformamide → HCID 178517534, compound

HRID 225455Notes

Reaction equation

HRID 225455 reaction equation
[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:13]=[CH:12][S:11][C:10]=2[C:14](O)=[O:15])=O)=[C:4]([F:20])[CH:3]=1.S(Cl)(Cl)=O.C[N:26](C=O)C>>[Cl:1][C:2]1[C:18]([F:19])=[CH:17][C:5]([C:6]2[NH:8][C:9]3[CH:13]=[CH:12][S:11][C:10]=3[C:14](=[O:15])[N:26]=2)=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57753058HCID 57753058, compound

Product 1

HCID 178517534HCID 178517534, compound

Conditions

Temperature
75 °C

Procedure

After a mixture of 3-[(4-chloro-2,5-difluorobenzoyl)amino]thiophene-2-carboxylic acid, thionyl chloride and DMF was stirred for 1.5 hours at 75° C., the solvent was removed under reduced pressure and 1,4-dioxane was added. After the reaction solution was added to 28% ammonia water under ice cooling and stirred at room temperature for 3 hours, the solvent was removed under reduced pressure. MeOH and 1M NaOH aq were added to the obtained residue and stirred for 2.5 hours at 90° C. to give 2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine-4(1H)-one.

Workup

  1. customthe solvent was removed under reduced pressure and 1,4-dioxane
  2. additionwas added
  3. additionAfter the reaction solution was added to 28% ammonia water under ice cooling
  4. stirringstirred at room temperature for 3 hours
  5. customthe solvent was removed under reduced pressure
  6. additionMeOH and 1M NaOH aq were added to the obtained residue
  7. stirringstirred for 2.5 hours at 90° C.

Sources & evidence

ORD record
ord-381fc32724bc401c91a6a692900299c0
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

Loading…