1H-Pyrazolo[3,4-d]pyrimidin-4-amine → HCID 178508725, compound

HRID 1500835Notes

Reaction equation

HRID 1500835 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[N:8][C:9]([NH2:10])=[C:4]2[CH:3]=[N:2]1.[I:11]NC(=O)CCC(N)=O>>[I:11][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:10])[NH:1][N:2]=1

Participants

3

Reactant 2

HCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 21864724N-Iodosuccinamide

Product 1

HCID 178508725HCID 178508725, compound

Procedure

Halogenation of commercially avalaible 1H-pyrazolo[3,4-d]pyrimidin-4-amine provides an entry into the synthesis of compounds of Formula (A), (B), (C) and/or (D). In one embodiment, 1H-pyrazolo[3,4-d]pyrimidin-4-amine is treated with N-iodosuccinamide to give 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. Metal catalyzed cross coupling reactions are then carried out on 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine. In one embodiment, palladium mediated cross-coupling of a suitably substituted phenyl boronic acid under basic conditions constructs intermediate 2. Intermediate 2 is coupled with N-Boc-3-hydroxypiperidine (as non-limiting example) via Mitsunobu reaction to give the Boc (tert-butyloxycarbonyl) protected intermediate 3. After deprotection with acid, coupling with, but not limited to, an acid chloride, such as, but not limited to, acryloyl chloride, completes the synthesis to give compound 4.

Sources & evidence

ORD record
ord-2874ce6188584399be80984598cd1800
Source dataset
uspto-grants-2015_12
Patent number
US09206189B2

Reaction notes

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