Cyclopentanol → 1-[2-cyclopentyloxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

HRID 600381Notes

Reaction equation

HRID 600381 reaction equation
[CH3:1][C:2]([CH3:24])([CH3:23])[C:3]([C:5]1[C:13]2[NH:12][C:11](=[O:14])[CH:10]=[N:9][C:8]=2[N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:6]=1)=[O:4].[CH:25]1(O)[CH2:29][CH2:28][CH2:27][CH2:26]1.C(P(CCCC)CCCC)CCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:25]1([O:14][C:11]2[N:12]=[C:13]3[C:5]([C:3](=[O:4])[C:2]([CH3:24])([CH3:23])[CH3:1])=[CH:6][N:7]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:20])([CH3:22])[CH3:21])[C:8]3=[N:9][CH:10]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 7298Cyclopentanol2×HCID 13831Tributylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 57831039HCID 57831039, compound

Product 1

HCID 578292191-[2-cyclopentyloxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-oneYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 7-(2,2-dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-1,5-dihydro-pyrrolo[2,3-b]pyrazin-2-one (0.029 g, 0.082 mmol), 1 mL of tetrahydrofuran, cyclopentanol (0.010 mL, 0.11 mmol), tributylphosphine (0.025 mL, 0.1 mmol), and diisopropyl azodicarboxylate (0.020 mL, 0.10 mmol) under nitrogen was stirred at 65° C. for 17.5 h then allowed to cool. Additional cyclopentanol (0.020 mL, 0.22 mmol), tributylphosphine (0.050 mL, 0.20 mmol), and diisopropyl azodicarboxylate (0.040 mL, 0.21 mmol) were added, and the solution stirred at 65° C. for 2.5 h. The yellow solution was partitioned between 5 mL of water and 5 mL of ethyl acetate. The organic layer was washed with 5 mL of a sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated to a yellow oil. Silica gel chromatography (10% EtOAc/hexanes) afforded 0.017 g (51%) of 1-[2-cyclopentyloxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a colorless oil.

Workup

  1. temperatureto cool
  2. customThe yellow solution was partitioned between 5 mL of water and 5 mL of ethyl acetate
  3. washThe organic layer was washed with 5 mL of a sat. aq. NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-9e425d8cd61040678b4e54a99bafd5ba
Source dataset
uspto-grants-2011_03
Patent number
US07902197B2

Reaction notes

Loading…