Diisopropylethylamine → HCID 178461602, compound

HRID 522807Notes

Reaction equation

HRID 522807 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:3]=1.C(N(C(C)C)CC)(C)C.Cl.[CH3:28][C@H:29]1[CH2:34][O:33][CH2:32][CH2:31][NH:30]1>CC(O)CC.C(Cl)Cl>[CH3:28][C@H:29]1[CH2:34][O:33][CH2:32][CH2:31][N:30]1[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@H:12]2[CH3:17])[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 53486469(3S)-3-Methylmorpholine--hydrogen chloride (1/1)HCID 178461592HCID 178461592, compound

Product 1

HCID 178461602HCID 178461602, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6568(+-)-2-ButanolSolvent

Conditions

Temperature
175 °C

Procedure

2-Chloro-6-((R)-3-methyl-morpholin-4-yl)-9H-purine (712 mg, 2.81 mmol), diisopropylethylamine (0.98 mL, 5.61 mmol), and (S)-3-methylmorpholin hydrochloride (579 mg, 4.21 mmol) were stirred in 2-butanol (3 mL) in a closed 5 mL microwave tube under argon at 50° C., until all ingredients were dissolved. The reaction was then stirred at 175° C. for 48 hours. The organic layer was diluted with 200 mL of CH2Cl2 and washed with brine. Drying over Na2SO4, filtering and concentration under reduced pressure gave a residue, which was purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aq NH3 in a gradient from 100/0/0.1 to 90/10/0.1) to give the product as a solid (588 mg, 66%).

Workup

  1. dissolutionwere dissolved
  2. washwashed with brine
  3. dry with materialDrying over Na2SO4
  4. filtrationfiltering
  5. concentrationconcentration under reduced pressure
  6. customgave a residue, which
  7. customwas purified by column chromatography (40 g SiO2, CH2Cl2/EtOH/aq NH3 in a gradient from 100/0/0.1 to 90/10/0.1)

Sources & evidence

ORD record
ord-695a09cf50ac47d7a23b94020bd86545
Source dataset
uspto-grants-2016_05
Patent number
US09334271B2

Reaction notes

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