Ammonia → HCID 57680886, compound

HRID 1028798Notes

Reaction equation

HRID 1028798 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[C:11]([I:12])=[CH:10][N:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:5]=2[N:6]=[CH:7][N:8]=1.C(=O)=O.CC(C)=O>O1CCOCC1.CC(O)C>[I:12][C:11]1[C:4]2[C:3]([NH2:1])=[N:8][CH:7]=[N:6][C:5]=2[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 57680997HCID 57680997, compound

Product 1

HCID 57680886HCID 57680886, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Gaseous ammonia (from a lecture bottle) was condensed into a suspension of 4-chloro-5-iodo-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine (30 mg, 0.084 mmol) in dioxane (2 mL) and iPrOH (2 mL) in a sealable glass tube, cooled by dry ice/acetone, until the volume increased by ≈2 mL, then the tube was sealed and heated to 100° C. overnight. The solvents were evaporated, water was added, the mixture was extracted with CH2Cl2 (3×30 mL), and the combined CH2Cl2 extracts were washed with brine, dried over MgSO4, filtered and concentrated to give the title compound as a white solid. 1H NMR (CDCl3, 400 MHz): δ=5.69 (brs, 2H), 7.36 (s, 1H), 7.36-7.41 (m, 1H), 7.49-7.55 (m, 2H), 7.60-7.64 (m, 2H), 8.33 (s, 1H). MS (ES+): m/z 337.0 (100) [MH+]. HPLC: tR=2.8 min (OpenLynx, polar—5 min).

Workup

  1. customcondensed
  2. temperatureincreased by ≈2 mL
  3. customthe tube was sealed
  4. customThe solvents were evaporated
  5. additionwater was added
  6. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  7. washthe combined CH2Cl2 extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9cb84d5c309c4c8bb0972b1ec0d7abd7
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

Loading…