Dichloromethane → 1-[9-Cyclopentyl-6-(3,4-dimethoxy-benzylamino)-9H-purin-2-yl]-piperidin-3-ol

HRID 1432378Notes

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[N:3]=1.Cl.[OH:29][CH:30]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>N1C=C(C)C=CC=1C>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([N:32]2[CH2:33][CH2:34][CH2:35][CH:30]([OH:29])[CH2:31]2)=[N:3][C:4]=3[NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Conditions

Temperature: 180 °C

Procedure

(2-Chloro-9-cyclopentyl-9H-purin-6-yl)-(3,4-dimethoxy-benzyl)-amine (446 mg, 1.15 mmol), 3-hydroxypiperidine hydrochloride (791 mg, 5.75 mmol) and K2CO3 (1.19 mg, 8.63 mmol) were suspended in 2,5-lutidine (10 mL) and the mixture was heated at 180° C. for 4 h. After cooling, CH2Cl2 (50 mL) was added and the solution was extracted with brine (2×15 mL). The organic fraction was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (95:5 CH2Cl2/MeOH) to afford the title compound as an off-white foam (427 mg, %). Anal. RP-HPLC (Phenomenex Jupiter, 5 μ, C18, 300 Å, 4.6×250 mm; 1 mL/min): tR=18.4 min (10-70% MeCN in 0.1% aq CF3COOH over 20 min); tR=16.0 min (35-45% MeCN in 0.1% aq CF3COOH over 20 min); purity>95% (λ=214 nm). DE-MALDI-TOF MS: [M+H]+=453.9 (C24H32N6O3=452.6).

Workup

temperatureAfter cooling
extractionthe solution was extracted with brine (2×15 mL)
dry with materialThe organic fraction was dried over MgSO4
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography (95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-903656498db8447eba1bf7e71be6e6fd
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612079B2

Reaction notes

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