Hydrochloric Acid → HCID 135522290, compound

HRID 1355389Notes

Reaction equation

HRID 1355389 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]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)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]3[CH2:20][CH2:21][NH:22][C:15]3=[N:14][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 136368748HCID 136368748, compound

Product 1

HCID 135522290HCID 135522290, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (R)-3-(5-acetoxyhexyl)-7,8-dihydro-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (700 mg, 2.0 mmol) and a 1.0 M solution of hydrogen chloride in diethyl ether (5 ml, 5.0 mmol) in methanol (100 ml) was stirred at room temperature overnight. After concentrating under reduced pressure, the residual solid was treated with ethyl acetate (20 ml) and stirred at room temperature for 2 hours. Filtration provided (R)-7,8-dihydro-3-(5-hydroxyhexyl)-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (CT-13430) (400 mg, 65% yield) as a white powder.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. additionthe residual solid was treated with ethyl acetate (20 ml)
  3. filtrationFiltration

Sources & evidence

ORD record
ord-0d2593fa2dfd436db3d8e95771982f8e
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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