Potassium Carbonate → HCID 117678149, compound

HRID 1778171Notes

Reaction equation

[C@H:1]12[CH2:24][C@H:4]([N:5]([C:7]3[N:12]=[C:11](S(C)(=O)=O)[N:10]=[C:9]([C:17]4[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=4)[CH:8]=3)[CH2:6]1)[CH2:3][O:2]2.C(=O)([O-])[O-].[K+].[K+].Cl.[CH:32]12[CH2:37][CH:35]([CH2:36]1)[CH2:34][NH:33]2>CS(C)=O>[CH:32]12[CH2:37][CH:35]([CH2:36]1)[CH2:34][N:33]2[C:11]1[N:10]=[C:9]([C:17]2[CH:18]=[N:19][C:20]([NH2:23])=[N:21][CH:22]=2)[CH:8]=[C:7]([N:5]2[CH2:6][C@@H:1]3[CH2:24][C@H:4]2[CH2:3][O:2]3)[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the mixture of 6-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-2-(methylsulfonyl)-[4,5′-bipyrimidin]-2′-amine (380 mg, 1.09 mmol) and potassium carbonate (754 mg, 5.45 mmol) in DMSO (5 mL) was added 2-azabicyclo[2.1.1]hexane hydrochloride (326 mg, 2.73 mmol). The mixture was stirred at 100° C. for 5 h. After removal of the solvent, the residue was purified by Prep-HPLC (formic acid) to afford 2-(2-azabicyclo[2.1.1]hexan-2-yl)-6-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)-[4,5′-bipyrimidin]-2′-amine (220 mg, 57% yield). LCMS (ESI): [MH]+=352.1; 1H NMR (400 MHz, DMSO-d6) δ 8.91 (s, 2H), 7.00 (s, 2H), 6.30-6.10 (m, 1H), 5.10-4.90 (m, 1H), 4.83 (d, J=6.4 Hz, 1H), 4.70-4.64 (m, 1H), 3.78-3.76 (m, 1H), 3.66-3.64 (m, 1H), 3.45-3.38 (m, 4H), 2.89-2.87 (m, 1H), 1.93-1.86 (m, 4H), 1.32-1.31 (m, 2H).

Workup

customAfter removal of the solvent
customthe residue was purified by Prep-HPLC (formic acid)

Sources & evidence

ORD record: ord-946c71e82991489ba2c08ea1810a72f0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266862B2

Reaction notes

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