3-(Dimethylamino)pyrrolidine → HCID 59333673, compound

HRID 421342Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:25][CH:26]2[CH2:28][CH2:27]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[C:18]([CH3:24])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=1)[N:5]=2.[CH3:29][N:30]([CH3:36])[CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1>CN1CCCC1=O>[CH:26]1([CH2:25][N:3]2[C:2]([N:33]3[CH2:34][CH2:35][CH:31]([N:30]([CH3:36])[CH3:29])[CH2:32]3)=[N:10][C:9]3[C:4]2=[N:5][C:6]([C:17]2[C:18]([CH3:24])=[N:19][C:20]([NH2:23])=[N:21][CH:22]=2)=[N:7][C:8]=3[N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 120 °C

Procedure

N-Methylpyrrolidone (1 ml) was 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 3-(dimethylamino)pyrolidine (285 mg, 2.49 mmol) and the resulting mixture was stirred at 120° C. for 3.5 hours. The reaction mixture was partitioned with chloroform and saturated brine and the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated under reduced pressure, then methylene chloride-ether was added to the residue, and the precipitate was collected by filtration, washed with ether, and dried under reduced pressure to give the title compound (55 mg, 46%) as a pale orange solid.

Workup

customThe reaction mixture was partitioned with chloroform and saturated brine
washthe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationThe solvent was concentrated under reduced pressure
additionmethylene chloride-ether was added to the residue
filtrationthe precipitate was collected by filtration
washwashed with ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-5e5902278c66408f81f866b935670eb0
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097622B2

Reaction notes

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