Cesium carbonate → HCID 90310726, compound

HRID 1519166Notes

Reaction equation

HRID 1519166 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[C:9]([F:19])=[C:10]([OH:18])[C:11]([CH:14]3[CH2:17][CH2:16][CH2:15]3)=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[Br:20][C:21]1[CH:22]=[N:23][C:24](Cl)=[N:25][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:20][C:21]1[CH:22]=[N:23][C:24]([O:18][C:10]2[C:9]([F:19])=[C:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=3)[CH:13]=[CH:12][C:11]=2[CH:14]2[CH2:15][CH2:16][CH2:17]2)=[N:25][CH:26]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 90311095HCID 90311095, compound

Product 1

HCID 90310726HCID 90310726, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial containing a stir-bar was added 3-(5-aminopyrazin-2-yl)-6-cyclobutyl-2-fluorophenol (100 mg, 0.386 mmol), 5-bromo-2-chloropyrimidine (74 mg, 0.39 mmol), cesium carbonate (188 mg, 0.580), and DMSO (2 mL). The vial was sealed and heated in the microwave for 30 minutes at 120° Celsius. The mixture was cooled to rt then passed through a syringe filter and the filtrate subjected to HPLC purification to give the title compound. 1H NMR (500 MHz, 2 mL) δ 8.69 (d, J=1.5, 2H), 8.24 (s, 1H), 8.10 (s, 1H), 7.79-7.69 (m, 1H), 7.27 (d, J=8.3, 1H), 3.72-3.58 (m, 1H), 2.23-2.10 (m, 3H), 2.02-1.94 (m, 1H), 1.89-1.75 (m, 1H).

Workup

  1. additionTo a microwave vial containing a stir-bar
  2. customThe vial was sealed
  3. temperatureThe mixture was cooled to rt
  4. customthen passed through a syringe
  5. filtrationfilter
  6. customthe filtrate subjected to HPLC purification

Sources & evidence

ORD record
ord-9276f0d658184c6da04d55faaf196a2c
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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