4-Methoxybenzylamine → HCID 57898118, compound

HRID 1693561Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([S:24]([CH3:27])(=[O:26])=[O:25])=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][N:37]=[C:36](Cl)[N:35]=3)=[CH:30][CH:29]=2)=[CH:4][CH:3]=1.[O:41]([C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1)[CH3:42]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([S:24]([CH3:27])(=[O:26])=[O:25])=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][N:37]=[C:36]([NH:48][CH2:47][C:46]4[CH:49]=[CH:50][C:43]([O:41][CH3:42])=[CH:44][CH:45]=4)[N:35]=3)=[CH:30][CH:29]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of crude 5-(4-chloro-phenyl)-6-[4-(2-chloro-pyrimidin-4-yl)-phenyl]-3-methanesulfonyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (from example 356) in EtOH (6 mL) is added 4-methoxylbenzylamine (0.4 mL). The mixture is heated at 100° C. for 24 h and then cooled down to room temperature. The precipitate is collected by filtration and washed with EtOH (2×3 mL). The solid is air dried for 14 h to provide the desired 5-(4-chloro-phenyl)-3-methanesulfonyl-6-{4-[2-(4-methoxy-benzylamino)-pyrimidin-4-yl]-phenyl}-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid (230 mg, 80%). HPLC-MS calculated C36H28ClN7O4S (M−H′): 690.2. Found: 690.2.

Workup

temperaturecooled down to room temperature
filtrationThe precipitate is collected by filtration
washwashed with EtOH (2×3 mL)
customdried for 14 h

Sources & evidence

ORD record: ord-29f0184b57e6421c8a279f675fbda5b3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158634B2

Reaction notes

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