Hydrochloric Acid → HCID 10308602, compound

HRID 1355401Notes

Reaction equation

HRID 1355401 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-e84d677c1154448393dcb57e9615be21
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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