Hydrochloric Acid → HCID 10308602, compound

HRID 1296409Notes

Reaction equation

HRID 1296409 reaction equation
C([O:4][C@H:5]([CH3:26])[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][CH2:23][C:15]3=[N:14][C:13]=2[N:12]([CH3:24])[C:11]1=[O:25])(=O)C.Cl.C(OCC)C>CO>[OH:4][C@H:5]([CH3:26])[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][CH2:23][C:15]3=[N:14][C:13]=2[N:12]([CH3:24])[C:11]1=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69153594HCID 69153594, compound

Product 1

HCID 10308602HCID 10308602, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-1-methyl-6,7,8,9-tetrahydro-pyrazino[2,1-f]purine-2,4(1H,3H)-dione (80 mg, 0.22 mmol) and a 1.0 M solution of hydrogen chloride in diethyl ether (1.0 ml, 1.0 mmol) in methanol (20 ml) was stirred at room temperature for 16 hours. After concentration under reduced pressure, the residue was purified by column chromatography on silica gel eluting with ethyl acetate-2.0 M methanolic ammonia (3:1) to provide (R)-3-(5-hydroxyhexyl)-1-methyl-6,7,8,9-tetrahydro-pyrazino[2,1-f]purine-2,4(1H,3H)-dione (CT-30099) (60 mg, 90% yield) as a white powder.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate-2.0 M methanolic ammonia (3:1)

Sources & evidence

ORD record
ord-f346354b256b4b0cac044020ded11519
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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