Water → 2,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 921322Notes

Reaction equation

HRID 921322 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[C:6]([Cl:13])[C:7]2[CH:12]=[CH:11][NH:10][C:8]=2[N:9]=1.[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl.O>CN(C=O)C>[Cl:3][C:4]1[N:5]=[C:6]([Cl:13])[C:7]2[CH:12]=[CH:11][N:10]([CH2:19][O:18][CH2:17][CH2:16][Si:15]([CH3:22])([CH3:21])[CH3:14])[C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 219764212,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (119 mg, 60% in oil, 2.98 mmol) in DMF (5 mL) was added 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (400 mg, 2.13 mmol) at 0° C. The resulting mixture was stirred for 30 min before 2-(trimethylsilyl)ethoxymethyl chloride (0.42 mL, 1.1 eq) was added. The mixture was then warmed up to room temperature and stirred for 1 hr. Water was added to quench the reaction. Extraction with CH2Cl2 followed by drying combined organic layers, evaporation, and chromatography on silica gel (20% EtOAc in heptane as eluent) gave the desired product in 84% yield (570 mg).

Workup

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionExtraction with CH2Cl2
  5. customby drying
  6. customlayers, evaporation, and chromatography on silica gel (20% EtOAc in heptane as eluent)

Sources & evidence

ORD record
ord-471970b051d445a58a7873c3d974699b
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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