1-(Methylsulfonyl)piperazine → HCID 59333658, compound

HRID 421308Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:24][CH:25]2[CH2:29][CH2:28][O:27][CH2:26]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.[S:30]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)([CH3:33])(=[O:32])=[O:31]>CS(C)=O>[CH3:33][S:30]([N:34]1[CH2:39][CH2:38][N:37]([C:2]2[N:3]([CH2:24][CH:25]3[CH2:29][CH2:28][O:27][CH2:26]3)[C:4]3[C:9]([N:10]=2)=[C:8]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[N:7]=[C:6]([C:17]2[CH:22]=[N:21][C:20]([NH2:23])=[N:19][CH:18]=2)[N:5]=3)[CH2:36][CH2:35]1)(=[O:32])=[O:31]

Participants

Conditions

Temperature: 150 °C

Procedure

Dimethyl sulfoxide (1 ml) was added to a mixture of 5-[8-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-2-yl]pyrimidin-2-amine (100 mg, 0.24 mmol) and N-mesylpiperazine (118 mg, 0.72 mmol) and the resulting mixture was stirred at 150° C. for 3 hours. The reaction mixture was cooled and then partitioned with chloroform and water, and the organic layer was washed with water again and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 25:1 to 20:1) to give the title compound (50 mg, 45%) as a pale yellow solid.

Workup

temperatureThe reaction mixture was cooled
custompartitioned with chloroform and water
washthe organic layer was washed with water again
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 25:1 to 20:1)

Sources & evidence

ORD record: ord-372f47b56e57494699e253293a74475c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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