Hydrochloric Acid → HCID 89630068, compound

HRID 882180Notes

Reaction equation

HRID 882180 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([CH:19]=[O:20])=[CH:17][N:16]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CC1C=CC(S([CH2:39][N+:40]#[C-:41])(=O)=O)=CC=1.[OH-].[K+].Cl>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[C:18]([C:19]4[O:20][CH:41]=[N:40][CH:39]=4)=[CH:17][N:16]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:12]=3[N:13]=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 161915Tosylmethyl isocyanideHCID 89630148HCID 89630148, compound

Product 1

HCID 89630068HCID 89630068, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To 4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde (135 mg, 0.339 mmol), tosmic (73 mg, 0.37 mmol) and potassium hydroxide (38 mg, 0.68 mmol), was added methanol (10 mL). The resulting solution was stirred for 12 hours at 25° C. and then the pH was adjusted to pH=6 with hydrogen chloride (1M aqueous solution). The reaction was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography using silica gel, eluting with 25% ethyl acetate/petroleum ether. The product was collected and concentrated in vacuo to afford 5-(4-(3-nitrophenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)oxazole as a yellow oil. LRMS (ESI) calc'd for C21H24N5O4Si [M+H]+: 438, found 438.

Workup

  1. extractionThe reaction was extracted with ethyl acetate (×3)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by chromatography
  7. washeluting with 25% ethyl acetate/petroleum ether
  8. customThe product was collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d330b1142644ec5bf18404596a75375
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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