Dimethyl Sulfide → HCID 44539807, compound

HRID 1520424Notes

Reaction equation

HRID 1520424 reaction equation
CSC.[CH:4]1([Mg]Br)[CH2:6][CH2:5]1.Br[CH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17](=[O:27])[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][N:22]=3)[N:20]=[C:11]12>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH:4]1([CH:10]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]3[C:17](=[O:27])[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][N:22]=4)[N:20]=[C:11]23)[CH2:6][CH2:5]1

Participants

7

Reactant 3

HCID 1068Dimethyl SulfideHCID 67177346HCID 67177346, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 44539807HCID 44539807, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 1.33 g (6.48 mmol) of CuBr.DMS in 25 mL of dry tetrahydrofuran at −78° C., was slowly added 12.45 mL (6.23 mmol) of cyclopropyl magnesium bromide (0.5 M in tetrahydrofuran). The resulting mixture was stirred at room temperature for 30 min. 0.800 g (2.49 mmol) of (+/−)-10-bromo-2-pyrimidin-4-yl-7,8,9,10-tetrahydro-6H-pyrimido[1,2-α]azepin-4-one dissolved in 10 mL of dry tetrahydrofuran was added at −78° C. and the resulting mixture was stirred for 1.5 hours and allowed to warm to room temperature. The mixture was dissolved in a saturated solution of ammonium chloride and ethyl acetate. The organic phases were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography (dichloromethane/methanol/ammoniac in proportions of 99/1/0.1) to afford 0.230 g (33%) of a white solid.

Workup

  1. customat −78° C.
  2. additionwas added at −78° C.
  3. stirringthe resulting mixture was stirred for 1.5 hours
  4. temperatureto warm to room temperature
  5. washThe organic phases were washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (dichloromethane/methanol/ammoniac in proportions of 99/1/0.1)

Sources & evidence

ORD record
ord-dab5ff6c3af44403b11ec5e8020ed7e2
Source dataset
uspto-grants-2015_07
Patent number
US09073914B2

Reaction notes

Loading…