HCID 18507607, compound → HCID 18507487, compound

HRID 1356092Notes

Reaction equation

HRID 1356092 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[C:5]([C:13]#[N:14])=[C:4]([S:15][CH3:16])[N:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]C[S-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[CH2:9])[C:5]([C:13]#[N:14])=[C:4]([S:15][CH2:16][CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=2)[N:3]=1

Participants

4

Reactant 2

HCID 18507607HCID 18507607, compoundHCID 23674037HCID 23674037, compound

Product 1

HCID 18507487HCID 18507487, compoundYield 1.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 200 mg (0.85 mmol) 2-amino-4-(1-ethoxy-vinyl)-6-methylsulfanyl-pyrimidine-5-carbonitrile in 16 ml dioxane was added 546 mg (3.38 mmol) sodium 2-pyridin-2-yl-ethanethiolate and the mixture heated at 100° C. for 1 hour. The reaction mixture was then concentrated in vacuo and the residue triturated in ether. The crystals were removed by filtration and the mother liquor concentrated in vacuo. The residue was then recrystallised from ethyl acetate/hexane and the crystals additionally purified by HPLC to afford 4.0 mg (1%) 2-amino-4-(1-ethoxy-vinyl)-6-(2-pyridin-2-yl-ethylsulfanyl)-pyrimidine-5-carbonitrile as an off-white crystalline solid. ES-MS m/e (%): 328 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue triturated in ether
  3. customThe crystals were removed by filtration
  4. concentrationthe mother liquor concentrated in vacuo
  5. customThe residue was then recrystallised from ethyl acetate/hexane
  6. customthe crystals additionally purified by HPLC

Sources & evidence

ORD record
ord-bae028ae893e403486cc865be840ba27
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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