Potassium Carbonate → HCID 15289174, compound

HRID 1018034Notes

Reaction equation

HRID 1018034 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[C:12][Si](C)(C)C)=[CH:9][N:8]([C@@H:17]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[CH2:18]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[CH:12])=[CH:9][N:8]([C@@H:17]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[CH2:18]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15289172HCID 15289172, compound

Product 1

HCID 15289174HCID 15289174, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg of compound (23) are dissolved in 20 ml of MeOH. Adding 8 mg of K2CO3 results in hydrolysis after 1 h of stirring. After the solution has been subjected to rotary evaporation, the residue is chromatographed on silica gel in the eluent methylene chloride/MeOH (8:1). Recrystallization from MeOH results in colorless crystals (73%). Calc. C 56.93, H 5.15, N 20.43; found C 56.77, H 5.71, N 20.42. 1H-NMR (DMSO): 8.13 (s, 1H, H-2), 7.81 (s, 1H, H-6), 6.65 (broad, 2H, NH2), 6.49 (t, 1H, H-1′), 5.25 (m, 1H, 3′-OH), 5.05 (m, 1H, 5′-OH), 4.36 (m, 1H, H-3′), 4.26 (s, 1H, ethyne), 3.84 (s, 1H, H-4′), 3.56 (m, 2H, H-5′), 2.47 (m, 1H, H-2′), 2.21 (m, 1H, H-2′).

Workup

  1. customresults in hydrolysis after 1 h
  2. customAfter the solution has been subjected to rotary evaporation
  3. customthe residue is chromatographed on silica gel in the eluent methylene chloride/MeOH (8:1)
  4. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-4e75dd095ec849ecb688e480d07a19fc
Source dataset
uspto-grants-2002_11
Patent number
US06479651B1

Reaction notes

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