3-(Phenylsulfonyl)pyrrolidine → 5-{9-(Cyclopropylmethyl)-6-morpholin-4-yl-8-[3-(phenylsulfonyl)pyrrolidin-1-yl]-9H-purin-2-yl}pyrimidin-2-amine

HRID 421340Notes

Reaction equation

[C:1]1([S:7]([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:16]1[N:17]([CH2:38][CH:39]2[CH2:41][CH2:40]2)[C:18]2[C:23]([N:24]=1)=[C:22]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[N:21]=[C:20]([C:31]1[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=1)[N:19]=2>CS(C)=O>[CH:39]1([CH2:38][N:17]2[C:16]([N:12]3[CH2:13][CH2:14][CH:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[CH2:11]3)=[N:24][C:23]3[C:18]2=[N:19][C:20]([C:31]2[CH:36]=[N:35][C:34]([NH2:37])=[N:33][CH:32]=2)=[N:21][C:22]=3[N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH2:40][CH2:41]1

Participants

Conditions

Temperature: 150 °C

Procedure

3-(Phenylsulfonyl)pyrrolidine (110 mg, 0.52 mmol) and dimethyl sulfoxide (0.8 ml) were added to 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine (80 mg, 0.21 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 silica gel chromatography (ethyl acetate:hexane=2:1) to give the title compound (20 mg, 17%) as a white 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 silica gel chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record: ord-0d6934cbb62e4987962d1aa74f928d5e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

Loading…