Sodium Methoxide → HCID 67428565, compound

HRID 1660754Notes

Reaction equation

HRID 1660754 reaction equation
Br[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12.[CH3:29][O-:30].[Na+]>CO.[Cu]I>[CH2:17]([CH:16]([C:15]1[N:10]2[N:9]=[C:8]([CH3:22])[C:7]([C:6]3[S:5][C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:3][C:2]=3[O:30][CH3:29])=[C:11]2[N:12]=[C:13]([CH3:21])[CH:14]=1)[CH2:19][CH3:20])[CH3:18]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67428983HCID 67428983, compound

Product 1

HCID 67428565HCID 67428565, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of 3-(4-bromo-2-morpholin-4-yl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (162 mg, 0.35 mmol), sodium methoxide (57 mg, 1.05 mmol) and copper(I) iodide (67 mg, 0.35 mmol) in methanol (3 mL) in a sealed 4-mL vial for 15 h at 120° C. Cool to room temperature, remove the solid by filtration, and concentrate the filtrate under vacuum. Purify the residue by flash chromatography, eluting with hexanes/THF (10/2). Recrystallize the material from methanol to give the title compound (20 mg). ES/MS m/z 416.0 (M+1)+.

Workup

  1. customremove the solid
  2. filtrationby filtration
  3. concentrationconcentrate the filtrate under vacuum
  4. customPurify the residue by flash chromatography
  5. washeluting with hexanes/THF (10/2)
  6. customRecrystallize the material from methanol

Sources & evidence

ORD record
ord-8c7023446dbc4642b27377b41b0e1a97
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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