Diisopropylethylamine → HCID 178461593, compound

HRID 1876618Notes

Reaction equation

HRID 1876618 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.C(N(CC)C(C)C)(C)C>C(O)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

5

Reactant 3

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

Product 1

HCID 178461593HCID 178461593, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol (5 ml) solution of 2,6-dichloro-9H-purine (187 mg, 0.99 mmol), (S)-3-methyl-morpholine (100 mg, 0.99 mmol), and N,N-diisopropylethylamine (252 μl, 1.48 mmol) was heated to reflux for 15 hours. The reaction mixture was returned to room temperature and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=98:2 to 97:3) to give the title compound (132 mg, 53%) as a solid.

Workup

  1. temperatureto reflux for 15 hours
  2. customwas returned to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=98:2 to 97:3)

Sources & evidence

ORD record
ord-73ea40097e54429585cf3235b3c6d61d
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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