Diisopropylethylamine → HCID 178461593, compound

HRID 1922868Notes

Reaction equation

HRID 1922868 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4](Cl)[N:3]=1.[CH3:12][C@H:13]1[CH2:18][O:17][CH2:16][CH2:15][NH:14]1.CCN(C(C)C)C(C)C>>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][C@@H:13]2[CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholineHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 178461593HCID 178461593, compoundYield 76%

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dichloro-9H-purine (5.2 g, 27.51 mmol), (S)-3-methylmorpholine (3.30 g, 32.62 mmol) and DIPEA (5.0 mL, 28.71 mmol) in IMS (130 mL) were heated at 80° C. for 3 h then stirred at r.t. for 17 h. The resulting white precipitate was collected by filtration and the filtrate concentrated in vacuo to a reduced volume and the resulting precipitate also collected by filtration. Both batches of solid were combined in DCM and the organic phase washed with H2O and brine, then dried (MgSO4) and concentrated in vacuo affording the title compound as a white powder (5.3 g, 76%). LCMS (method H): RT 2.54 min [M+H]+ 254.1

Workup

  1. filtrationThe resulting white precipitate was collected by filtration
  2. concentrationthe filtrate concentrated in vacuo to a reduced volume
  3. filtrationthe resulting precipitate also collected by filtration
  4. washthe organic phase washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57637e05791d4d52850ed0ace4fa42dd
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

Loading…