Hydrochloric Acid → 2-(Butyloxy)-9-(4-piperidinylmethyl)-9H-purin-6-amine hydrochloride

HRID 1044948Notes

Reaction equation

HRID 1044948 reaction equation
[ClH:1].[NH2:2][C:3]1[N:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:9]=[C:8]2[C:4]=1[N:5]=[C:6](OC)[N:7]2[CH2:17][CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1>O1CCOCC1.CO>[ClH:1].[CH2:13]([O:12][C:10]1[N:9]=[C:8]2[C:4]([N:5]=[CH:6][N:7]2[CH2:17][CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)=[C:3]([NH2:2])[N:11]=1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 583060912-Butoxy-9-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-8-methoxyadenine

Product 1

HCID 671801992-(Butyloxy)-9-(4-piperidinylmethyl)-9H-purin-6-amine hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4N hydrogen chloride in dioxane (5.3 mL) was added to a solution of 1,1-dimethylethyl 4-{[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]methyl}-1-piperidinecarboxylate (630 mg) in methanol (16 mL). After 4.5 hours at room temperature, the reaction mixture was concentrated and dried under high vacuum. Purification by chromatography on silica gel eluting with a gradient of chloroform/methanol/water 90:10:1 to 75:25:1 afforded the title compound as a white solid (404 mg).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customdried under high vacuum
  3. customPurification by chromatography on silica gel eluting with a gradient of chloroform/methanol/water 90:10:1 to 75:25:1

Sources & evidence

ORD record
ord-4e2bf0b0aa2a49478465fe2449809df0
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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