Diisopropylethylamine → 5-{8-[4-(Methylsulfonyl)piperidin-1-yl]-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl}pyrimidin-2-amine

HRID 1876553Notes

Reaction equation

Cl.[CH3:2][S:3]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)(=[O:5])=[O:4].C(N(C(C)C)CC)(C)C.Cl[C:22]1[N:23]([CH2:44][C:45]([F:48])([F:47])[F:46])[C:24]2[C:29]([N:30]=1)=[C:28]([N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[N:27]=[C:26]([C:37]1[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=1)[N:25]=2>CN1CCCC1=O>[CH3:2][S:3]([CH:6]1[CH2:11][CH2:10][N:9]([C:22]2[N:23]([CH2:44][C:45]([F:46])([F:48])[F:47])[C:24]3[C:29]([N:30]=2)=[C:28]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[N:27]=[C:26]([C:37]2[CH:42]=[N:41][C:40]([NH2:43])=[N:39][CH:38]=2)[N:25]=3)[CH2:8][CH2:7]1)(=[O:5])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

4-Methanesulfonylpiperidine hydrochloride (385 mg, 1.93 mmol), diisopropylethylamine (672 μg, 3.9 mmol), and N-methyl-2-pyrrolidone (2 ml) were added to 5-[8-chloro-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine (200 mg, 0.48 mmol) and the resulting mixture was stirred at 100° C. for 12 hours. The reaction mixture was partitioned with ethyl acetate 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=20:1) to give the title compound (81 mg, 33%) as a pale yellow solid.

Workup

customThe reaction mixture was partitioned with ethyl acetate 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=20:1)

Sources & evidence

ORD record: ord-60f648b9e241441aa96cbe1cf561e8d7
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309546B2

Reaction notes

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