Water → 4-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-yl)-cyclohexanecarboxylic acid ethyl ester

HRID 1505706Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9](OS(C)(=O)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:17][N:18]1[CH:22]=[C:21]([C:23]2[CH:24]=[C:25]([C:29]3[N:34]=[CH:33][C:32]([C:35]4[CH:36]=[N:37][NH:38][CH:39]=4)=[CH:31][N:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH:20]=[N:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([N:37]2[CH:36]=[C:35]([C:32]3[CH:31]=[N:30][C:29]([C:25]4[CH:26]=[CH:27][CH:28]=[C:23]([C:21]5[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=5)[CH:24]=4)=[N:34][CH:33]=3)[CH:39]=[N:38]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

4-Methanesulfonyloxy-cyclohexanecarboxylic acid ethyl ester (AOKChem Co., Ltd; 689 mg; 2.75 mmol; 1.04 eq.) in DMF (5 mL) was added in one portion to a suspension of 2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1H-pyrazol-4-yl)pyrimidine (example 3, 104 mg; 0.34 mmol; 1.0 eq.) and cesium carbonate (2.35 g; 7.21 mmol; 2.7 eq.) in DMF (10 mL). The reaction mixture was heated in MW at 120° C. for 35 min. It was then poured into water and filtered. The resulting solid was triturated with ACN to give the title compound as a yellow solid (264 mg, 17%). 1H NMR (300 MHz, DMSO-d6) δ 9.16 (s, 2H), 8.57-8.46 (m, 2H), 8.26 (s, 1H), 8.24-8.18 (m, 1H), 8.13 (s, 1H), 7.92 (s, 1H), 7.77-7.66 (m, 1H), 7.51 (t, J=7.8 Hz, 1H), 4.32-3.99 (m, 3H), 3.89 (s, 3H), 2.48-2.34 (m, 1H), 2.23-1.48 (m, 8H), 1.27-1.14 (m, 3H). MS (ESI+): 457.3.

Workup

filtrationfiltered
customThe resulting solid was triturated with ACN

Sources & evidence

ORD record: ord-cac0148eaa884994a41afcd9e300d762
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216991B2

Reaction notes

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