rel-(2R,6S)-2,6-dimethylpiperazine → HCID 59333627, compound

HRID 421317Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.Cl[C:10]1[N:11]([CH2:33][CH:34]2[CH2:36][CH2:35]2)[C:12]2[C:17]([N:18]=1)=[C:16]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[N:15]=[C:14]([C:25]1[C:26]([CH3:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1)[N:13]=2>CN1CCCC1=O>[CH:34]1([CH2:33][N:11]2[C:10]([N:6]3[CH2:5][C@H:4]([CH3:8])[NH:3][C@H:2]([CH3:1])[CH2:7]3)=[N:18][C:17]3[C:12]2=[N:13][C:14]([C:25]2[C:26]([CH3:32])=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)=[N:15][C:16]=3[N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:35][CH2:36]1

Participants

Conditions

Temperature: 150 °C

Procedure

cis-2,6-Dimethylpiperazine (114 mg, 1.0 mmol) and N-methylpyrrolidone (1 ml) were added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]-4-methylpyrimidin-2-amine (100 mg, 0.25 mmol) and the resulting mixture was stirred at 150° C. for 4 hours. The reaction mixture was partitioned with ethyl acetate and water and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (90 mg, 75%) as a light brown solid.

Workup

customThe reaction mixture was partitioned with ethyl acetate and water
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record: ord-d674b1f001bf4ccc9ccea6b0ef35ef2f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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