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

HRID 1429710Notes

Reaction equation

HRID 1429710 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 available 1H-pyrazolo[3,4-d]pyrimidin-4-amine provides an entry into the synthesis of compounds of Formula (A1-A6), (B1-B6), (C1-C6) and/or (D1-D6). 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 13.

Workup

  1. custominto the synthesis of compounds of Formula (A1-A6), (B1-B6), (C1-C6) and/or (D1-D6)

Sources & evidence

ORD record
ord-189b5baf6c054116bcf5d067da203c3b
Source dataset
uspto-grants-2015_01
Patent number
US08940750B2

Reaction notes

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