3,4-dihydro-2H-pyran → N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

HRID 2368177Notes

Reaction equation

HRID 2368177 reaction equation
FC1C=C(NC2N=C3NN=CC3=C([C:24]3[CH:25]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:27]=[CH:28][CH:29]=3)N=2)C=CC=1N1CCOCC1.ClC1N=C(Cl)N=C2NN=CC=12.O1C=CCCC1.Cl[C:53]1[N:58]=[C:57]([Cl:59])[N:56]=[C:55]2[N:60]([CH:63]3[CH2:68][CH2:67][CH2:66][CH2:65][O:64]3)[N:61]=[CH:62][C:54]=12.C(NC1C=C(B(O)O)C=CC=1)(=O)C=C>>[Cl:59][C:57]1[N:56]=[C:55]2[N:60]([CH:63]3[CH2:68][CH2:67][CH2:66][CH2:65][O:64]3)[N:61]=[CH:62][C:54]2=[C:53]([C:28]2[CH:27]=[C:26]([NH:30][C:31](=[O:34])[CH:32]=[CH2:33])[CH:25]=[CH:24][CH:29]=2)[N:58]=1

Participants

6

Reactant 5

HCID 80803,4-dihydro-2H-pyranHCID 103213313-Acrylamidophenylboronic acidHCID 120664494,6-Dichloro-1H-pyrazolo(3,4-d)pyrimidineHCID 576542774,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidineHCID 68388406N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Product 1

HCID 86677518N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide

Procedure

As an example, N-(3-(6-((3-fluoro-4-morpholinophenyl)amino)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide can be prepared according to Route II. Beginning with 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine, protection can be accomplished by reaction with 3,4-dihydro-2H-pyran. The resulting 4,6-dichloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine can then be coupled with (3-acrylamidophenyl)boronic acid under palladium catalyzed conditions to provide N-(3-(6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide.

Sources & evidence

ORD record
ord-26edbd882ca744558807d9f96f93becf
Source dataset
uspto-grants-2014_04
Patent number
US08703767B2

Reaction notes

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