Piperidine → 2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(1-piperidinyl)pentyl]-9H-purin-6-amine

HRID 1616282Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]([O:16][CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10]([O:19][C@@H:20]([CH3:24])[CH2:21][CH2:22][CH3:23])=[N:11][C:12]=2[NH2:18].C(N(CC)CC)C.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C=O)C>[CH3:24][C@H:20]([O:19][C:10]1[N:9]=[C:8]2[C:13]([N:14]=[C:15]([O:16][CH3:17])[N:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:12]([NH2:18])[N:11]=1)[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

9-(5-Chloropentyl)-2-{[(15)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine (80 mg, 0.225 mmol), triethylamine (0.031 ml, 0.225 mmol) and piperidine (0.045 ml, 0.45 mmol) were suspended in DMF (3 ml) and the mixture heated to 70° C. for 18 hours. The solvent was removed and the residue partitioned between DCM (4 ml) and saturated sodium bicarbonate (4 ml). The aqueous phase was re-extracted with further DCM and the combined organic extracts were concentrated and the residue dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP (Method A). The product -containing fractions were combined and evaporated under a stream of nitrogen to give the title compound (47.2 mg).

Workup

customThe solvent was removed
customthe residue partitioned between DCM (4 ml) and saturated sodium bicarbonate (4 ml)
extractionThe aqueous phase was re-extracted with further DCM
concentrationthe combined organic extracts were concentrated
dissolutionthe residue dissolved in 1:1 MeOH
customDMSO (1 ml) and purified by MDAP (Method A)
customevaporated under a stream of nitrogen

Sources & evidence

ORD record: ord-68d8b479097d45b88f07a189a987d413
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765772B2

Reaction notes

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