Chloromethyl ethyl ether → HCID 69154097, compound

HRID 1355414Notes

Reaction equation

HRID 1355414 reaction equation
[C:1]([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[N:16]3[CH2:20][CH2:21][NH:22][C:15]3=[N:14][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:35]([O:37][CH2:38]Cl)[CH3:36]>C(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[N:16]3[CH2:20][CH2:21][N:22]([CH2:38][O:37][CH2:35][CH3:36])[C:15]3=[N:14][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 136368748HCID 136368748, compound

Product 1

HCID 69154097HCID 69154097, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirring solution of (R)-3-(5-acetoxyhexyl)-7,8-dihydro-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (3.5 g, 10.0 mmol) and diisopropylethylamine (10.32 g, 80 mmol) in chloroform (100 ml) was added chloromethyl ethyl ether (3.78 g, 40 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to provide (R)-3-(5-acetoxyhexyl)-7,8-dihydro-8-ethoxymethyl-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (2.0 g, 49% yield).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-5139e13e24334882ac3a87ee5a4b3382
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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