Methanol → methyl 4-chloro-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

HRID 2208124Notes

Reaction equation

HRID 2208124 reaction equation
[Cl:1][C:2]1[C:3]2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:10]([CH3:20])=[C:9]([CH:21]=[O:22])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[C-]#N.[K+].[CH3:26][OH:27]>O=[Mn]=O>[Cl:1][C:2]1[C:3]2[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[C:10]([CH3:20])=[C:9]([C:21]([O:27][CH3:26])=[O:22])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9032Potassium CyanideHCID 866666394-Chloro-2,6-dimethyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde

Product 1

HCID 86666640methyl 4-chloro-2,6-dimethyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

To a well stirred mixture of 4-chloro-2,6-dimethyl-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde from example A10 (9.49 g; 27.90 mmol), MeOH (50 mL), KCN (6.00 g; 92.10 mmol) and MnO2 (35.60 g, 383.30 mmol) acetic acid (1.68 g; 27.90 mmol) is added at ambient temperature. After 4 hours the dark mixture is filtered through Celite and the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane:ethylacetate/9:1) affording the title compound as an pale yellow oil.

Workup

  1. additionis added at ambient temperature
  2. filtrationAfter 4 hours the dark mixture is filtered through Celite
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel (cyclohexane:ethylacetate/9:1)

Sources & evidence

ORD record
ord-1625e8f8214c46f983631d0a8b6d750c
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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