Sodium methanethiolate → N-(2,2-diphenylethyl)-2-(methylsulphanyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 2268405Notes

Reaction equation

HRID 2268405 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH:17][CH2:18][CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.[CH3:32][S-:33].[Na+]>CN(C)C=O.O>[C:20]1([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:18][NH:17][C:4]2[N:3]=[C:2]([S:33][CH3:32])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 101813352-Chloro-N-(2,2-diphenylethyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 21978277N-(2,2-diphenylethyl)-2-(methylsulphanyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 99.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of 2-chloro-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (preparation 6) (49.7 g, 0.11 mol) in dry N,N-dimethylformamide (200 ml) was treated with sodium thiomethoxide (10 g, 0.14 mol) and the resulting mixture heated under an atmosphere of nitrogen at 100° C. for 1.5 hr. The mixture was then stirred at room temperature for 72 hr and then reheated to 100° C. for a further 2 hr. The reaction mixture was then cooled and diluted with water (1000 ml). A suspension was formed which was extracted with diethyl ether (×2). The combined organic extracts were washed sequentially with water and brine, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was dissolved in diethyl ether and the solvent removed under reduced pressure. This procedure was then repeated using pentane to afford the title compound as a foam (48.9 g).

Workup

  1. waitreheated to 100° C. for a further 2 hr
  2. temperatureThe reaction mixture was then cooled
  3. customA suspension was formed which
  4. extractionwas extracted with diethyl ether (×2)
  5. washThe combined organic extracts were washed sequentially with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. dissolutionThe residue was dissolved in diethyl ether
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e10953dea5ea4110b27a849146b8c0c0
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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