Diisopropylethylamine → HCID 178461592, compound

HRID 1922860Notes

Reaction equation

HRID 1922860 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 641498(R)-3-MethylmorpholineHCID 1784188752,6-dichloro-1H-purine

Product 1

HCID 178461592HCID 178461592, compoundYield 31.2%

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-dichloro-9H-purine (2.18 g, 11.53 mmol), (R)-3-methylmorpholine (1.40 g, 13.84 mmol) and DIPEA (2.57 mL, 14.99 mmol) in IMS (50 mL) were heated at 80° C. for 8 h. The reaction mixture was concentrated in vacuo to a reduced volume and the residue partitioned between EtOAc and H2O. The organic phase was dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%) affording the title compound as an off-white solid (914 mg, 31%). LCMS (method H): RT 2.53 min [M+H]+ 254.3

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to a reduced volume
  2. customthe residue partitioned between EtOAc and H2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-10%)

Sources & evidence

ORD record
ord-912f5c96cd85468ab1a649ed76594103
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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