Sodium Carbonate → 5-(1-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)pyrimidin-4-amine

HRID 1186797Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](B(O)O)=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Br[C:21]1[C:22]([NH2:27])=[N:23][CH:24]=[N:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO.COCCOC.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([C:21]4[C:22]([NH2:27])=[N:23][CH:24]=[N:25][CH:26]=4)=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Example 8 was prepared according to the general procedure of Example 1, except that the reaction mixture was heated at 105° C. for 2.25 h, and using the following materials: Intermediate 5A (38.0 mg, 0.148 mmol), 5-bromopyrimidin-4-amine (55.2 mg, 0.317 mmol), sodium carbonate (59.2 mg, 0.559 mmol), degassed EtOH:DME:H2O (1.2:2.5:1.0 ratio) (1.5 mL) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol). Example 8 was isolated as a white solid (15.2 mg, 33.0%). Purification was done by preparative HPLC (Condition A) using a Phenomenex Luna Axia 30×100 mm S10 column from 10% Solvent B to 90% Solvent B over 12 min, ret. T=7.4 min. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.65-8.85 (1 H, m), 8.44-8.60 (1 H, m), 8.21-8.39 (4 H, m), 7.36-7.52 (3 H, m), 6.95 (2 H, br. s.). LC/MS (Condition B): ret. T=2.22 min, (M+H)+ 307.05. Analytical HPLC: (Condition A): >98%, ret. T=18.63 min, (Condition B): >99%, ret. T=19.30 min, (Condition C): >99%, ret. T=7.15 min, (Condition D): >99%, ret. T=7.56 min.

Workup

customExample 8 was prepared

Sources & evidence

ORD record: ord-b591c9e097004733a5cc05f57dfb642f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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