Potassium Carbonate → HCID 58541963, compound

HRID 1966780Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4F)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.C[N:31]1[CH2:35][N:34]=[CH:33][NH:32]1.[C:36]([O-])([O-])=O.[K+].[K+]>CS(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:29]=[CH:28][C:11]3[N:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:31]4[CH:35]=[N:34][C:33]([CH3:36])=[N:32]4)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-fluoro-benzonitrile (200 mg, 0.52 mmol) in DMSO (6 mL) are added 2-methyl-1H-1,2,4-triazole (65 mg, 0.78 mmol) and K2CO3 (143 mg, 1.04 mmol) at room temperature. The solution is heated at 100° C. for 12 hours. The solution is cooled down and extracted with EtOAc (2×15 mL) and H2O (20 mL). The combined organic layer is dried with MgSO4 (500 mg) and filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent to afford the title compound (130 mg, 56%) as a white solid. LCMS (ESMS): m/z: 450.20 (M++1)

Workup

temperatureThe solution is cooled down
extractionextracted with EtOAc (2×15 mL) and H2O (20 mL)
dry with materialThe combined organic layer is dried with MgSO4 (500 mg)
filtrationfiltered
concentrationThe filtrate is concentrated
customthe residue is purified by silica gel flash column chromatography with 5% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record: ord-82dfceef6629476ea417b57e746c58ce
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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