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Hydrochloric Acid → HCID 10150076, compound

HRID 1355411
Notes
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Reaction equation

HRID 1355411 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
HCID 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 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-ff3b00ba7cf0405f847914fff69de957
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06586429B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes