Potassium Carbonate → HCID 90310763, compound

HRID 1519180Notes

Reaction equation

HRID 1519180 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]([F:21])=[C:10]([OH:20])[C:11]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:12][CH:13]=2)=[N:6][CH:7]=1.Cl[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[CH:14]1([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=3)=[C:9]([F:21])[C:10]=2[O:20][C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 744042-ChloropyrimidineHCID 90310682HCID 90310682, compound

Product 1

HCID 90310763HCID 90310763, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture consisting of 3-(5-aminopyrazin-2-yl)-6-cyclohexyl-2-fluorophenol (0.05 g, 0.2 mmol), 2-chloropyrimidine (0.025 g, 0.22 mmol), K2CO3 (0.05 g, 0.4 mmol), and 18-crown-6 (0.01 g, 0.04 mmol), and DMSO (2 mL) was heated via microwave irradiation for 1 hour at 120° Celsius. After cooling to room temperature, the reaction mixture was filtered and purified directly via HPLC to yield the title compound (42 mg, 65%). MS (ESI): mass calcd. for C20H20FN5O, 365.17; m/z found, 366.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.63-8.60 (m, 2H), 8.28-8.24 (m, 1H), 8.20-8.18 (m, 1H), 7.80-7.76 (m, 1H), 7.31-7.23 (m, 2H), 2.81-2.74 (m, 1H), 1.83-1.68 (m, 5H), 1.53-1.43 (m, 2H), 1.35-1.24 (m, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. custompurified directly via HPLC

Sources & evidence

ORD record
ord-5ef278794de1466f8e5d9b726bd7abc5
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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