Cesium fluoride → HCID 67509209, compound

HRID 2172867Notes

Reaction equation

HRID 2172867 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.ClC1C(C2C(C)=CC=CN=2)=NC(S(C)=O)=NC=1.[CH3:36][S:37]([CH2:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)(=[O:39])=[O:38].[F-].[Cs+]>CS(C)=O.O.CCOC(C)=O.CO.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:4][C:5]([N:44]2[CH2:45][CH2:46][CH:41]([CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:42][CH2:43]2)=[N:6][CH:7]=1

Participants

10

Reactant 4

HCID 25953Cesium fluorideHCID 22275402HCID 22275402, compoundHCID 67508142HCID 67508142, compoundHCID 67508565HCID 67508565, compound

Product 1

HCID 67509209HCID 67509209, compoundYield 46%

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfonyl)pyrimidine and 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfinyl)pyrimidine (300 mg, 1.05 mmol) in DMSO (15 mL) was added 4-(methylsulfonylmethyl)piperidine (440 mg, 1.65 mmol) and CsF (640 mg, 4.2 mmol). The resulting mixture was heated at 100° C. at microwave for 30 min. TLC (CH2Cl2:MeOH=10:1) indicated that the reaction was complete. The mixture was then treated with EtOAc (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was then extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was purified via prep. HPLC to give title compound (183 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.47-8.48 (d, 1H), 8.28 (s, 1H), 7.55-7.56 (dd, 1H), 7.20-7.24 (m, 1H), 4.66-4.69 (d, 1H), 2.88-2.92 (m, 7H), 2.30-2.34 (m, 1H), 2.18 (s, 3H), 1.94-1.97 (m, 2 H), 1.26-1.37 (m, 2H); m/z for C17H21ClN4O2S 381.4 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was then extracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified via prep

Sources & evidence

ORD record
ord-3163ab5e50fc4c02b6f54cb96f0ce303
Source dataset
uspto-grants-2015_06
Patent number
US09056865B2

Reaction notes

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