2-(2-Bromoethyl)-1,3-dioxolane → HCID 68828677, compound

HRID 1782147Notes

Reaction equation

HRID 1782147 reaction equation
[NH2:1][CH:2]([C:6]1[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8](=[O:16])[C:9]2[C:14]([CH3:15])=[N:13][S:12][C:10]=2[N:11]=1)[CH:3]([CH3:5])[CH3:4].Br[CH2:25][CH2:26][CH:27]1[O:31][CH2:30][CH2:29][O:28]1>CN(C=O)C.O>[CH2:17]([N:7]1[C:8](=[O:16])[C:9]2[C:14]([CH3:15])=[N:13][S:12][C:10]=2[N:11]=[C:6]1[CH:2]([NH:1][CH2:25][CH2:26][CH:27]1[O:31][CH2:30][CH2:29][O:28]1)[CH:3]([CH3:5])[CH3:4])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 54757413HCID 54757413, compound

Product 1

HCID 68828677HCID 68828677, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-(1-amino-2-methyl-propyl)-5-benzyl-3-methyl-5H-isothiazolo[5,4-d]pyrimidin-4-one (method 30) (1.6 g, 4.88 mmol) in anhydrous DMF (20 mL), 2-(2-bromo-ethyl)-[1,3]dioxolane (0.88 g, 4.88 mmol) was added and the resulting solution was heated at 70° C. for 2 h. The reaction mixture was cooled, diluted with water and extracted with EtOAc (3×60 mL). The combined organic extracts were dried (Na2SO4) and concentrated to provide the crude product (2 g), which was used as such in the next reaction. m/z 429 (MH+); 1H-NMR (300 MHz) δ 0.88 (d, 3H), 0.96 (d, 3H), 1.54-1.62 (m, 2H), 1.86-2.05 (m, 2H), 2.18 (bs, 1H), 2.38-2.46 (m, 1H), 2.84 (s, 3H), 3.57 (d, 1H), 3.74-3.94 (m, 4H), 4.78 (t, 1H), 4.99 (d, 1H), 5.85 (d, 1H), 7.15-7.38 (m, 5H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (3×60 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f987da265dd4e879f128a121cab73a6
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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