HCID 21922569, compound → HCID 21922567, compound

HRID 1244762Notes

Reaction equation

HRID 1244762 reaction equation
[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([N:11](COCC[Si](C)(C)C)[C:12]([C:16]([C:18]4[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=4)=[O:17])=[N:13]3)=[C:9]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>C(O)C.Cl>[N:1]1([C:7]2[N:15]=[C:14]3[C:10]([NH:11][C:12]([C:16]([C:18]4[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=4)=[O:17])=[N:13]3)=[C:9]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 21922569HCID 21922569, compound

Product 1

HCID 21922567HCID 21922567, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

[2,6-Di-morpholin-4-yl-7-(2-trimethylsilanyl-ethoxymethyl)-7H-purin-8-yl]-m-tolyl-methanone (185 mg, 0.34 mmol) was dissolved in ethanol (10 ml) and 2N HCl (4 mL). The resulting suspension was heated to reflux for 4 hrs then cooled to room temperature. After neutralization with 2N NaOH, ethanol was removed under reduced pressure and ethyl acetate (100 mL) was added. The ethyl acetate layer was washed with water (3×50 mL), dried over MgSO4 then evaporated to dryness. The crude product was purified by silcagel column chromatography. Elution with a gradient of 25% ethyl aceate/hexane to ethyl acetate to 10% methanol/ethyl aceate produced (2,6-di-morpholin-4-yl-7H-purin-8-yl)-m-tolyl-methanone (80 mg, 57% yield).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 4 hrs
  3. customAfter neutralization with 2N NaOH, ethanol was removed under reduced pressure and ethyl acetate (100 mL)
  4. additionwas added
  5. washThe ethyl acetate layer was washed with water (3×50 mL)
  6. dry with materialdried over MgSO4
  7. customthen evaporated to dryness
  8. customThe crude product was purified by silcagel column chromatography
  9. washElution with a gradient of 25% ethyl aceate/hexane to ethyl acetate to 10% methanol/ethyl aceate

Sources & evidence

ORD record
ord-e63fe0abfe47491abac2cd86fe975418
Source dataset
uspto-grants-2006_10
Patent number
US07122665B2

Reaction notes

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