Sodium hydride → 6-Chloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-2-amine

HRID 1024074Notes

Reaction equation

HRID 1024074 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]([NH2:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether2×HCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 866841516-Chloro-9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purin-2-amineYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-9H-purin-2-amine (5.0 g, 29.6 mmol) and NaH (1.43 g, 32.5 mmol) in DMF (30 mL) was stirred at room temperature for 0.5 h. (2-(Chloromethoxy)ethyl)trimethylsilane (SEMCl, CAS Reg. No. 76513-69-4, 4.91 g, 29.6 mmol) was added and the resulting mixture was stirred at room temperature for 1.0 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 3:1 petroleum ether/ethyl acetate to afford 117a (5.1 g, 58%) as a yellow solid. MS-ESI: [M+H]+ 300.1

Workup

  1. addition76513-69-4, 4.91 g, 29.6 mmol) was added
  2. filtrationIt was then filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica-gel column chromatography
  5. washeluting with 3:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-b33230922b6d4928b89be61d6561ca48
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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