Sodium Carbonate → HCID 86677062, compound

HRID 518256Notes

Reaction equation

[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](B(O)O)[CH:11]=1.B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[Cl:1][C:2]1[C:7]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-Chloro-5-(pyridin-3-yl)pyrimidin-2-amine 131 was prepared from the coupling of 4-chloro-5-iodopyrimidin-2-amine with pyridin-3-ylboronic acid as follows: the amine (150 mg, 0.587 mmol), and the boronic acid (144 mg, 1.174 mmol) were suspended in dioxane (2.5 mL) and Na2CO3 (783 μA, 1.174 mmol) The mixture was bubbled with Ar for 5 min then charged with Pd(Ph3P)4 (136 mg, 0.117 mmol). The mixture was stirred at 90° C. for 2 h, then cooled to room temperature. The mixture was partitioned between EtOAc and water. The organic layer was dried, filtered, and concentrated to give a residue which was purified by silica gel column chromatography to give 4-chloro-5-(pyridin-3-yl)pyrimidin-2-amine 131.

Workup

temperaturecooled to room temperature
customThe mixture was partitioned between EtOAc and water
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated
customto give a residue which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-91527d9fd9c746b4b669f51c2032944c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115141B2

Reaction notes

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