Potassium Acetate → HCID 117678232, compound

HRID 1778180Notes

Reaction equation

HRID 1778180 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(#N)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[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

7

Reactant 3

HCID 517044Potassium AcetateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 117678044HCID 117678044, compound

Product 1

HCID 117678232HCID 117678232, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (1S,4S)-5-(6-chloro-2-methylsulfonyl-pyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2.1]heptane (500 mg, 1.73 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (382 mg, 1.73 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (63.8 mg, 0.0863 mmol) in acetonitrile (6.90 mL) was added potassium acetate in water (3.45 mL) in a microwave vial equipped with a stirbar. The mixture was microwaved at 110° C. for 5 min. The solid was and washed with ethyl acetate (5 mL) filtered under vacuum, providing 6-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-2-(methylsulfonyl)-[4,5′-bipyrimidin]-2′-amine (598 mg, crude). 1H NMR (400 MHz, DMSO-d6) δ 9.02 (d, J=5.6, 2.8 Hz, 2H), 7.40-6.97 (m, 1H), 7.28 (s, 2H), 5.14 (d, J=16.0 Hz, 1H), 4.76 (d, J=27.9 Hz, 1H), 3.82 (d, J=7.7, 1.5 Hz, 1H), 3.76-3.66 (m, 1H), 3.60-3.51 (m, 1H), 3.50-3.41 (m, 1H), 3.35 (d, J=6.1 Hz, 3H), 1.95 (d, J=22.0 Hz, 2H).

Workup

  1. customvial equipped with a stirbar
  2. customThe mixture was microwaved at 110° C. for 5 min
  3. washwashed with ethyl acetate (5 mL)
  4. filtrationfiltered under vacuum

Sources & evidence

ORD record
ord-67bce6b8725c47769c4f3e672feb5675
Source dataset
uspto-grants-2016_02
Patent number
US09266862B2

Reaction notes

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