1,2-Diaminocyclohexane → 1-(3-Pyrrol-1-yl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

HRID 655860Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][CH:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.C1(N)CCCCC1N.[NH:21]1[C:25]2=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]2[CH:23]=[N:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu](I)I.C(OCC)(=O)C>[N:8]1([C:4]2[CH:3]=[C:2]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]4[CH:23]=[N:22]3)[CH:7]=[CH:6][CH:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9]1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(3-Bromo-phenyl)-1H-pyrrole (0.3 g, 1.0 eq, 1.35 mmol) and cyclohexane-1,2-diamine (0.03 g, 0.2 eq, 0.27 mmol) were added to a pre-stirred mixture of 1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine (0.22 g, 1.2 eq, 1.62 mmol), copper iodide (0.013 g, 0.5 eq, 0.68 mmol) and potassium phosphate (0.6 g, 2.1 eq, 2.84 mmol) in DMF (8 ml) under an inert atmosphere. The reaction mixture was then stirred at 110° C. for 24 hours, and allowed to cool to room temperature. Ethyl acetate (8 ml) was then added to the reaction mixture which was then filtered through a plug of silica, which was then washed with a further portion of ethylacetate (20 ml). The filtrate was concentrated to dryness in vacuo and the resultant residue was purified by column chromatography using DCM/MeOH (95:5) as eluent to yield the title compound as an off-white solid (18 mg, 0.07 mmol, 5%). LCMS: [M+H]+=277, Rt=1.80 min, 97% purity.

Workup

temperatureto cool to room temperature
filtrationwas then filtered through a plug of silica, which
washwas then washed with a further portion of ethylacetate (20 ml)
concentrationThe filtrate was concentrated to dryness in vacuo
customthe resultant residue was purified by column chromatography

Sources & evidence

ORD record: ord-0d9436e56cf44cc5b3abb6d01f4d37fa
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071607B2

Reaction notes

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