Hydrochloric Acid → HCID 70872130, compound

HRID 2281661Notes

Reaction equation

HRID 2281661 reaction equation
C[N:2]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=1)[C:3]1[C:4]2[CH:12]=[C:11]([CH3:13])[O:10][C:5]=2[N:6]=[C:7]([CH3:9])[N:8]=1.[H-].[Na+].S(OC)(OC)(=O)=O.Cl>CCOC(C)=O.CCCCCC.CN(C=O)C>[CH3:9][C:7]1[N:8]=[C:3]([NH:2][C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=2)[C:4]2[CH:12]=[C:11]([CH3:13])[O:10][C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 70872056HCID 70872056, compound

Product 1

HCID 70872130HCID 70872130, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

N,2,6-Trimethyl-N-[4-(methylsulfanyl)phenyl]furo[2,3-d]pyrimidin-4-amine (Composition No. 125) To a 25 mL round bottom flask was weighed N (143 mg, 0.5 mmol) and was added DMF (2 mL) to afford a solution. The flask was purged with argon for five min followed by cooling down to 0° C. using ice bath. Sodium hydride (36 mg, 1.5 mmol) was added to the solution at 0° C. The solution was stirred for 30 min at 0° C. under argon atmosphere. Dimethyl sulfate (150 mg, 1.2 mmol) was introduced to the reaction mixture with the help of a syringe and the flask was warmed to room temperature. The mixture was stirred at room temperature for another 3 h at the end of which 1 N hydrochloric acid (5 mL) was added carefully to quench the reaction. The reaction solvent was removed under reduced pressure and the residue was suspended in water (20 mL). The suspension was extracted using ethyl acetate (10 mL×2). Combined organic extracts were washed with brine (10 mL) dried (anhydrous sodium sulfate) and concentrated under reduced pressure. Silica gel (200 mg) was added and solvent evaporated to afford a plug. Column chromatography by elution with hexane:ethyl acetate (5:1) afforded 78 mg (52%) of Composition No. 125 as a light yellow solid: Rf 0.5 (AcOEt/Hexane, 1:3); 1H NMR (DMSO-d6) δ 2.18 (s, 3H), 2.49 (s, 3H), 2.54 (s, 3H), 3.47 (s, 3H), 4.73 (s, 1H), 7.30-7.32 (d, 2H,), 7.38-7.39 (d, 2H); Anal. Calcd. for C16H17N3OS: C, 64.19; H, 5.72; N, 14.04, S, 10.71. Found C, 64.26; H, 5.68; N, 13.90, S, 10.80.

Workup

  1. custom125) To a 25 mL round bottom flask was weighed
  2. customto afford a solution
  3. customThe flask was purged with argon for five min
  4. temperaturethe flask was warmed to room temperature
  5. additionwas added carefully
  6. customto quench
  7. customthe reaction
  8. customThe reaction solvent was removed under reduced pressure
  9. extractionThe suspension was extracted
  10. washCombined organic extracts were washed with brine (10 mL)
  11. dry with materialdried (anhydrous sodium sulfate)
  12. concentrationconcentrated under reduced pressure
  13. additionSilica gel (200 mg) was added
  14. customsolvent evaporated
  15. customto afford a plug
  16. washColumn chromatography by elution with hexane:ethyl acetate (5:1)
  17. customafforded 78 mg (52%) of Composition No

Sources & evidence

ORD record
ord-d8896b5f57b04cae9b56a6c655a03819
Source dataset
uspto-grants-2015_09
Patent number
US09139590B2

Reaction notes

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