Sodium methanethiolate → HCID 19371733, compound

HRID 129470Notes

Reaction equation

HRID 129470 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([NH:13][C:14]1[C:19](Br)=[C:18]([CH2:21][CH3:22])[N:17]=[CH:16][N:15]=1)[CH3:12].[CH3:23][S-:24].[Na+]>CN1CCCC1=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([NH:13][C:14]1[C:19]([S:24][CH3:23])=[C:18]([CH2:21][CH3:22])[N:17]=[CH:16][N:15]=1)[CH3:12]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 19371739HCID 19371739, compound

Product 1

HCID 19371733HCID 19371733, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.99 g (0.014 mol) of 4-[1'-(β-naphthyl)-ethylamino]-5-bromo-6-ethylpyrimidine are dissolved in 18 ml of N-methylpyrrolidone, and the solution is heated at 60° C. with 3.2 g of sodium methanethiolate (CH3SNa) for 5 hours. The mixture is then extracted with water and ethyl acetate, the extract is washed and the solvent is removed using a rotary evaporator. Purification by chromatography on silica gel (eluant: 3 parts ethyl acetate and 7 parts hexane) yields, in addition to the starting product, 1.42 g of pure substance in the form of a colourless oil. Analysis: C19H21N3S (M=323.46).

Workup

  1. extractionThe mixture is then extracted with water and ethyl acetate
  2. washthe extract is washed
  3. customthe solvent is removed
  4. customa rotary evaporator
  5. customPurification by chromatography on silica gel (eluant: 3 parts ethyl acetate and 7 parts hexane)
  6. customyields, in addition to the starting product, 1.42 g of pure substance in the form of a colourless oil

Sources & evidence

ORD record
ord-8ded1f7646a8483fb49dfb50d2724539
Source dataset
uspto-grants-1995_11
Patent number
US05468751

Reaction notes

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