Chloromethyl ethyl ether → HCID 69154097, compound

HRID 1296422Notes

Reaction equation

HRID 1296422 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-16cfcf58bbbe493497ff9bd2a554b1b4
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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