Tert-Butylamine → 5-tert-butyl-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

HRID 546447Notes

Reaction equation

HRID 546447 reaction equation
Br[CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1[CH2:8]Br.[C:10]([NH2:14])([CH3:13])([CH3:12])[CH3:11]>O1CCOCC1>[C:10]([N:14]1[CH2:8][C:7]2[S:6][CH:5]=[N:4][C:3]=2[CH2:2]1)([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 108496984,5-Bis(bromomethyl)thiazole

Product 1

HCID 184428165-tert-butyl-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4,5-bis(bromomethyl)thiazole (1.50 g) synthesized in 1) of Referential Example 109 was dissolved in dioxane (30 ml), and a dioxane solution (10 ml) of tert-butylamine (2.03 ml) was added dropwise to the solution over 1 hour at room temperature. After stirring at room temperature for 5 hours, the reaction mixture was concentrated, and dichloromethane and a saturated aqueous solution of sodium hydrogencarbonate were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:19) to obtain 5-tert-butyl-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole (407 mg) as a pale yellow oil.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondichloromethane and a saturated aqueous solution of sodium hydrogencarbonate were added to the residue
  3. customto separate an organic layer
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:19)

Sources & evidence

ORD record
ord-e285d966ec4948fea9053bb1d85c2d8d
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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