1,4-Cyclohexanedimethanamine → N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine

HRID 715606Notes

Reaction equation

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])[N:6]2[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.[NH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH:30]([CH2:33][NH2:34])[CH2:29][CH2:28]1>O1CCOCC1>[NH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][CH:30]([CH2:33][NH:34][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[N:6]3[C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-chloro-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purine (78 mg, 0.21 mmol, 1 eq.) in 2 mL of dioxane was added [4-(aminomethyl)cyclohexyl]methanamine (89 mg, 0.62 mmol, 2 eq.). The reaction was heated to 80° C. for 16 h. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography using 0-100% CMA 80/ethyl acetate to yield 76 mg (76%) of N-{[4-(aminomethyl)cyclohexyl]methyl}-8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-amine which was carried forward. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.85-1.13 (m, 2 H) 1.40-1.72 (m, 8 H) 1.74-2.01 (m, 2 H) 2.85-3.15 (m, 2H) 3.48-3.75 (m, 2H) 4.25-4.74 (m, 2 H) 5.98 (br. s., 1 H) 7.05-7.59 (m, 8 H) 8.44 (s, 1H).

Workup

concentrationThe reaction was concentrated in vacuo
customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-82bc77579c1c40a89f45a9937350b874
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187480B2

Reaction notes

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