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

HRID 1168280Notes

Reaction equation

HRID 1168280 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 solution of 2-chloro-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine (Preparation 2) (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 was heated under an atmosphere of nitrogen at 100° C. for 90 minutes. The mixture was stirred at room temperature for 72 hours and then reheated to 100° C. for a further 2 hours. The reaction mixture was cooled and diluted with water (1000 ml). A suspension was formed which was extracted with two portions of diethyl ether (1000 ml). The combined organic layers were washed sequentially with water and brine, dried (anhydrous magnesium sulphate), filtered and evaporated under reduced pressure. The residue was azeotroped from diethyl ether and then pentane to afford the title compound as a foam (48.9 g).

Workup

  1. waitreheated to 100° C. for a further 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customA suspension was formed which
  4. extractionwas extracted with two portions of diethyl ether (1000 ml)
  5. washThe combined organic layers were washed sequentially with water and brine
  6. dry with materialdried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was azeotroped from diethyl ether

Sources & evidence

ORD record
ord-f493a0119c884b2682174718cc48150d
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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