Hydrochloric Acid → 3-Chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

HRID 1893413Notes

Reaction equation

HRID 1893413 reaction equation
[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][C:5]2=[N:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68007751tert-butyl 3-chloro-5H,6H,7H,8H-imidazo[1,2-a]pyrazine-7-carboxylate

Product 1

HCID 654391243-Chloro-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl 3-chloro-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate (I19) (1.55 g, 6.01 mmol) and 4N HCl in 1,4-dioxane (6.01 mmol) was stirred at RT in 1,4-dioxane (5 mL) for 16 h. Solvents were removed in vacuo and the residue was loaded on to SCX (Varian 2×10 g) in methanol. The columns were washed with methanol and basic products eluted with 2M ammonia/methanol. The basic fractions were concentrated in vacuo to afford product in 913 mg that was used in subsequent steps without further purification.

Workup

  1. customSolvents were removed in vacuo
  2. washThe columns were washed with methanol and basic products
  3. washeluted with 2M ammonia/methanol
  4. concentrationThe basic fractions were concentrated in vacuo
  5. customto afford product in 913 mg that
  6. customwas used in subsequent steps without further purification

Sources & evidence

ORD record
ord-31ad87abc3b94c9db0b7eee583915f43
Source dataset
uspto-grants-2013_08
Patent number
US08513248B2

Reaction notes

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