Water → 2-[6-(Methylsulfanyl)pyrimidin-4-yl]acetonitrile

HRID 220077Notes

Reaction equation

HRID 220077 reaction equation
COC(=O)[CH:4]([C:13]#[N:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[N:8]=[CH:7][N:6]=1.[Na+].[Cl-].O>CS(C)=O>[CH3:12][S:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]([CH2:4][C:13]#[N:14])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 59173478Methyl cyano[6-(methylthio)-4-pyrimidinyl]acetate

Product 1

HCID 591732732-[6-(Methylsulfanyl)pyrimidin-4-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A Smith vial (10-20 mL) is charged with cyano-(6-methylsulfanyl-pyrimidin-4-yl)-acetic acid methyl ester (0.83 g, 3.72 mmol), NaCl (1.0 g), water (1 mL) and DMSO. The vial is sealed and irradiated at 160° C. for 50 minutes in Smith Synthesizer. The reaction mixture is partitioned between ethyl acetate and brine, and then filtered through a pad of celite and washed with ethyl acetate. The organic layer is separated and washed with brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by silica gel flash chromatography eluting with ethyl acetate in hexanes from 10% to 100% to afford (6-methylsulfanyl-pyrimidin-4-yl)-acetonitrile: 1H NMR 400 MHz (CDCl3) δ 8.93 (s, 1H), 7.47 (s, 1H), 4.20 (s, 2H), 2.56 (s, 3H); MS m/z 166.00 (M+1).

Workup

  1. customThe vial is sealed
  2. customirradiated at 160° C. for 50 minutes in Smith Synthesizer
  3. customThe reaction mixture is partitioned between ethyl acetate and brine
  4. filtrationfiltered through a pad of celite
  5. washwashed with ethyl acetate
  6. customThe organic layer is separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by silica gel flash chromatography
  12. washeluting with ethyl acetate in hexanes from 10% to 100%

Sources & evidence

ORD record
ord-a91a83c7bd484bd68b2465bef86b95d3
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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