Methanol → HCID 118023948, compound

HRID 2171795Notes

Reaction equation

HRID 2171795 reaction equation
[CH3:1][OH:2].[H-].[Na+].[Br:5][C:6]1[S:16][C:9]2[N:10]=[C:11]([CH3:15])[N:12]=[C:13](Cl)[C:8]=2[CH:7]=1.O>C1COCC1>[Br:5][C:6]1[S:16][C:9]2[N:10]=[C:11]([CH3:15])[N:12]=[C:13]([O:2][CH3:1])[C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 1180240846-Bromo-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile

Product 1

HCID 118023948HCID 118023948, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixed solution of MeOH (2 mL) and THF (15 mL) was cooled in an ice bath, and NaH (60% oil, 600 mg) was added thereto, followed by stirring for 15 minutes. Then, a solution of 6-bromo-4-chloro-2-methylthieno[2,3-d]pyrimidine (2.0 g) in THF (5 mL) was added thereto, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain 6-bromo-4-methoxy-2-methylthieno[2,3-d]pyrimidine (1.8 g).

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-9760c96b7ca74b87a56742f3af6c857e
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

Loading…