Dimethylformamide → HCID 86662295, compound

HRID 2364003Notes

Reaction equation

HRID 2364003 reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH3:13])([CH3:12])[N:5]([CH3:14])[C:4]=2[CH:3]=1.C([Li])CCC.CCCCCC.CN([CH:29]=[O:30])C>C1COCC1.[Cl-].[Na+].O.O>[CH3:14][N:5]1[C:4]2[CH:3]=[C:2]([CH:29]=[O:30])[S:10][C:9]=2[C:8](=[O:11])[NH:7][C:6]1([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 667439846-bromo-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-oneHCID 178418339Butyllithium

Product 1

HCID 86662295HCID 86662295, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred suspension of 6-bromo-1,2,2-trimethyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one (259 mg, 0.941 mmol) in THF (10 mL) at −78° C. was added dropwise 1.6 M n-butyllithium in hexane (1.29 mL, 2.07 mmol). After 20 min, DMF (0.146 mL, 1.88 mmol) was added, and the mixture was allowed to −30° C. for 30 min. The mixture was poured into water (50 mL) and brine (50 mL). Extraction with EtOAc (100 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave the title compound (205 mg, 97%) as yellow solid:

Workup

  1. waitthe mixture was allowed to −30° C. for 30 min
  2. extractionExtraction with EtOAc (100 mL)
  3. washwashing with brine
  4. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-84a19d9114854e9b89134bcfb704ca3f
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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