Hydrochloric Acid → HCID 135546597, compound

HRID 1296398Notes

Reaction equation

HRID 1296398 reaction equation
C([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]=[C:15]3[NH:20][CH2:21][CH2:22][N:14]3[C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=O)C.Cl.C(OCC)C>CO>[OH: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]=[C:15]3[NH:20][CH2:21][CH2:22][N:14]3[C:13]=2[N:12]([CH3:23])[C:11]1=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 136386013HCID 136386013, compound

Product 1

HCID 135546597HCID 135546597, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-1-methyl-1,6,7,8-tetrahydro-2H-imidazo[1,2-e]-purine-2,4(3H)-dione (100 mg, 0.286 mmol) and a 1.0 M solution of hydrogen chloride in diethyl ether (1 ml, 1.0 mmol) in methanol (25 ml) was stirred at room temperature overnight. After concentrating under reduced pressure, the residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol-chloroform (4:2:1) to provide (R)-3-(5-hydroxyhexyl)-1-methyl-1,6,7,8-tetrahydro-2H-imidazo[1,2-e]-purine-2,4(3H)-dione (CT-30268) (40 mg, 46% yield) as a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate-methanol-chloroform (4:2:1)

Sources & evidence

ORD record
ord-f37a66f1d4fa4dad942acd26afbeb4a4
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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