rel-(2R,6S)-2,6-dimethylpiperazine → HCID 59333510, compound

HRID 421335Notes

Reaction equation

Cl[C:2]1[N:3]([C@H:24]2[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25]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]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[CH3:33][C@H:34]1[CH2:39][NH:38][CH2:37][C@@H:36]([CH3:40])[NH:35]1>CS(C)=O>[CH3:33][C@H:34]1[NH:35][C@@H:36]([CH3:40])[CH2:37][N:38]([C:2]2[N:3]([C@H:24]3[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:25]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:22]=[N:21][C:20]([NH2:23])=[N:19][CH:18]=2)[N:5]=3)[CH2:39]1

Participants

Conditions

Temperature: 140 °C

Procedure

Dimethyl sulfoxide (1 ml) was added to 5-{8-chloro-9-[(3S)-1-(methylsulfonyl)pyrrolidin-3-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (100 mg, 0.21 mmol) and cis-2,6-dimethylpiperazine (119 mg, 1.04 mmol) and the resulting mixture was stirred at 140° C. for 1 hour. The reaction mixture was partitioned with chloroform and water, the organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=9:1) to give the title compound (95 mg, 82%) as a light brown solid.

Workup

customThe reaction mixture was partitioned with chloroform and water
dry with materialthe organic layer was dried over magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record: ord-71128ee491a94493b8b855d528881d62
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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