Sodium Carbonate → HCID 117678232, compound

HRID 1778170Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[N:5]=[C:4]([N:12]2[CH2:17][C@@H:16]3[CH2:18][C@H:13]2[CH2:14][O:15]3)[CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][C:30]([NH2:33])=[N:31][CH:32]=2)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[C@H:16]12[CH2:18][C@H:13]([N:12]([C:4]3[N:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[N:7]=[C:2]([C:27]4[CH:28]=[N:29][C:30]([NH2:33])=[N:31][CH:32]=4)[CH:3]=3)[CH2:17]1)[CH2:14][O:15]2

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave vial charged with (1S,4S)-5-(6-chloro-2-(methylsulfonyl)pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]-heptane (600 mg, 2.07 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (641 mg, 2.90 mmol), potassium acetate (284 mg, 2.90 mmol) and sodium carbonate (307 mg, 2.90 mmol) in acetonitrile/water (1 (5:1, 6.0 mL) was added PdCl2{PtBu2(Ph-p-NMe2)}2 (147 mg, 0.21 mmol) under nitrogen. The vial was sealed and heated by microwave irradiation at 140° C. for 40 min. The reaction mixture was concentrated in vacuo, and resulting residue was purified by flash column chromatography (5% methanol in dichloromethane) to provide 6-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-2-(methylsulfonyl)-[4,5′-bipyrimidin]-2′-amine (380 mg, 52.7% yield). LCMS (ESI): [MH]+=349.0.

Workup

customThe vial was sealed
concentrationThe reaction mixture was concentrated in vacuo
customresulting residue
customwas purified by flash column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-3296052d61534271bb0f2531db2ed96f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266862B2

Reaction notes

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