Ethyl Acetate → 2-chloro-8-(methylsulfonyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

HRID 929189Notes

Reaction equation

HRID 929189 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:8]2)=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH2:29][O:28][CH2:27][CH2:26][Si:25]([CH3:32])([CH3:31])[CH3:24])[C:7]([S:11]([CH3:14])(=[O:13])=[O:12])=[N:8]2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 900418402-chloro-8-(methylsulfonyl)-7H-purine

Product 1

HCID 900424992-chloro-8-(methylsulfonyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-chloro-8-(methylsulfonyl)-7H-purine (570 mg, 2.45 mmol) and N,N-diisopropylethylamine (3.42 mL, 19.60 mmol) in anhydrous DMF (16.7 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride (2.17 mL, 12.25 mmol). The reaction was stirred under N2 at RT for 20 h, then added to EtOAc (1.0 L) and washed with saturated NH4Cl (0.2 L). The aqueous layer was separated and back-extracted with EtOAc (0.2 L). The organic layers combined and evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 24 g silica RediSep Rf® Gold column and employing a 0-40% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C12H19ClN4O3SSi 362.06 observed m/e: 385.30 (M+23)′ (Rt 1.33/2.0 min)

Workup

  1. washwashed with saturated NH4Cl (0.2 L)
  2. customThe aqueous layer was separated
  3. extractionback-extracted with EtOAc (0.2 L)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6abdc0f627f740abaf8547fe576d7159
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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