Hydrochloric Acid → HCID 10150076, compound

HRID 1296419Notes

Reaction equation

HRID 1296419 reaction equation
[C:1]([N:4]1[C:8]2=[N:9][C:10]3[N:11]([CH3:32])[C:12](=[O:31])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([O:23][Si](C(C)(C)C)(C)C)[CH3:22])[C:14](=[O:16])[C:15]=3[N:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.C(OCC)C.C(N(CC)CC)C>CO.O>[C:1]([N:4]1[C:8]2=[N:9][C:10]3[N:11]([CH3:32])[C:12](=[O:31])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([OH:23])[CH3:22])[C:14](=[O:16])[C:15]=3[N:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 69155257HCID 69155257, compound

Product 1

HCID 10150076HCID 10150076, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of (R)-8-acetyl-7,8-dihydro-1-methyl-3-(5-tert-butyldimethylsilyloxyhexyl)-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (200 mg, 0.43 mmol) in methanol (20 ml) was added a 1.0 M solution of hydrogen chloride in diethylether (0.4 ml, 0.40 mmol). After stirring at room temperature for 30 minutes, the reaction mixture was treated with triethyamine (0.1 ml). Concentration under reduced pressure gave a white solid which was treated with water (20 ml) and stirred for 1 hour. The solid was filtered, washed with water, and dried under vacuum to provide (R)-8-acetyl-7,8-dihydro-3-(5-hydroxyhexyl)-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (CT-30260) (135 mg, 90% yield) as a white powder.

Workup

  1. concentrationConcentration under reduced pressure
  2. customgave a white solid which
  3. stirringstirred for 1 hour
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b0dc9861cba1425d87047e4d5d1daef8
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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