Ammonia → 3-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine

HRID 2402609Notes

Reaction equation

HRID 2402609 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([CH:12]3[CH2:15][CH2:14][CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.[NH3:16]>CC(O)C>[CH:12]1([C:8]2[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:16])[C:3]3=[C:10]([I:11])[N:9]=2)[CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 426093648-Chloro-3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazine

Product 1

HCID 426093653-Cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
115 °C

Procedure

A Parr bomb containing 8-chloro-3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazine (759 mg, 2.3 mmol) in IPA (100 mL) was saturated with NH3(g) for 5 min at 0° C. then sealed and heated at 115° C. for 38 h. The reaction mixture was then concentrated under reduced pressure, partitioned between DCM (200 mL) and H2O (50 mL) and extracted with DCM (50 mL). Combined organic fractions were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to provide the title compound as a white solid; 1H NMR (400 MHz, CDCl3) δ 7.13 (d, J=4.8 Hz, 1H), 7.01 (d, J=5.2 Hz, 1H), 5.63 (br, 2H), 3.73 (quintetd, J=0.8 Hz, 8.4 Hz, 1H), 2.60-2.38 (m, 4H), 2.20-1.90 (m, 2H); MS (ES+): m/z 315.9 (100) [MH+]; HPLC: tR=1.75 min (OpenLynx, polar—5 min).

Workup

  1. customthen sealed
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. custompartitioned between DCM (200 mL) and H2O (50 mL)
  4. extractionextracted with DCM (50 mL)
  5. washCombined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8a34ca7784a4c9f835a5d872f98ad6d
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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