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

HRID 11757Notes

Reaction equation

HRID 11757 reaction equation
[Cl:1][C:2]1[NH:7][C:6]2=[N:8][CH:9]=[CH:10][C:5]2=[C:4]([Cl:11])[N:3]=1.[H-].[Na+].[CH3:14][Si:15]([CH2:18][CH2:19]Cl)([CH3:17])[CH3:16].[OH2:21].[CH3:22]C#N>>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][N:8]([CH2:22][O:21][CH2:19][CH2:18][Si:15]([CH3:17])([CH3:16])[CH3:14])[C:6]=2[N:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 11040763(2-Chloroethyl)trimethylsilaneHCID 178418895HCID 178418895, compound

Product 1

HCID 219764212,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineYield 104%

Procedure

A solution of 2,4-dichloro-1H-pyrrolo[2,3-d]pyrimidine (542 mg, 2.58 mmol) in MeCN (20 mL) was treated with NaH (113 mg, 2.84 mmol), stirred for 1 h, treated with trimethylsilylethyl chloride (502 μL, 2.84 mmol), stirred at room temperature for 3 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (913 mg, 104%) which was used crude in the next reaction.

Workup

  1. stirringstirred at room temperature for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4602b66e6fc3458f9668186fafd743ef
Source dataset
uspto-grants-2006_08
Patent number
US07098333B2

Reaction notes

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