rel-(2R,6S)-2,6-dimethylpiperazine → HCID 59333514, compound

HRID 421324Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:25][CH:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[C:4]2[C:9]([N:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[N:7]=[C:6]([C:17]1[CH:18]=[N:19][C:20]([NH:23][CH3:24])=[N:21][CH:22]=1)[N:5]=2.[CH3:31][C@H:32]1[CH2:37][NH:36][CH2:35][C@@H:34]([CH3:38])[NH:33]1>CS(C)=O>[CH3:31][C@H:32]1[NH:33][C@@H:34]([CH3:38])[CH2:35][N:36]([C:2]2[N:3]([CH2:25][CH:26]3[CH2:30][CH2:29][O:28][CH2:27]3)[C:4]3[C:9]([N:10]=2)=[C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:7]=[C:6]([C:17]2[CH:18]=[N:19][C:20]([NH:23][CH3:24])=[N:21][CH:22]=2)[N:5]=3)[CH2:37]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-[8-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]-N-methylpyrimidin-2-amine (100 mg, 0.23 mmol), cis-2,6-dimethylpiperazine (80 mg, 0.70 mmol), and dimethyl sulfoxide (1 ml) was stirred at 150° C. for 2 hours. The mixture was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (64 mg, 54%) as a light brown solid.

Workup

customThe mixture was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record: ord-d8bbef194b384a0f90a40eae1a452152
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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