1-Phenethylamine, (-)- → 6-dimethylamino-2-(4-fluorophenyl)-3-[2-(1-(S)-phenylethylamino)-pyrimidin-4yl]-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one

HRID 7653

Reaction equation

[CH3:1][N:2]([CH3:29])[CH:3]1[CH2:7][N:6]2[C:8](=[O:28])[C:9]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13](S(C)(=O)=O)[N:12]=3)[N:5]2[CH2:4]1.[CH3:30][C@H:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:29])[CH:3]1[CH2:7][N:6]2[C:8](=[O:28])[C:9]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:38][C@H:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH3:30])[N:12]=3)[N:5]2[CH2:4]1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of the crude 6-dimethylamino-2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one, 25, prepared as described herein above (4.2 g, 10 mmol) and (S)-(−)-α-methyl-benzyl amine (45.2 mL, 351 mmol) are dissolved in toluene (100 mL). The resulting mixture is heated to 140° C. for 12 hours, cooled to room temperature and the solvent removed in vacuo. The resulting residue is purified over silica (1:1 EtOAc/hexanes) to afford the desired product.

Workup

temperaturecooled to room temperature
customthe solvent removed in vacuo
customThe resulting residue is purified over silica (1:1 EtOAc/hexanes)

Sources & evidence

ORD record: ord-d25374737a9e4104a2fb69a179eedfcd
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087615B2

Linked notes

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