Methyl iodide → HCID 59173431, compound

HRID 220080Notes

Reaction equation

HRID 220080 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:13]=[N:12][NH:11][C:10]=2[NH2:14])[CH:4]=1.[CH3:15][O-].[Na+].IC>>[CH3:15][N:12]1[CH:13]=[C:9]([C:5]2[CH:4]=[C:3]([S:2][CH3:1])[N:8]=[CH:7][N:6]=2)[C:10]([NH2:14])=[N:11]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 59173266HCID 59173266, compound

Product 1

HCID 59173431HCID 59173431, compound

Procedure

To the solution of 4-(6-Methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine (245 mg, 1.18 mmol) is added with NaOMe solution (25 wt % in MeOH, 425 μL, 1.53 mmol) dropwise. The reaction mixture is kept stirring for 30 minutes. Then Iodomethane (110 uL, 1.76 mmol) is added into the reaction mixture drop wise. After stirring overnight at room temperature, the reaction mixture is concentrated, treated with 75 mL ethyl acetate, and washed with water. Filtration removes the undissolved solid. The obtained filtrate is separated, and the collected organic layer is dried over sodium sulfate, and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 25% to 100% to afford 1-Methyl-4-(6-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.73 (s, 1H), 8.27 (s, 1H), 7.44 (s, 1H), 5.81 (s, 1H), 3.65 (s, 3H), 2.53 (s, 3H); MS m/z 222.07 (M+1).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. concentrationthe reaction mixture is concentrated
  3. additiontreated with 75 mL ethyl acetate
  4. washwashed with water
  5. filtrationFiltration
  6. customremoves the undissolved solid
  7. customThe obtained filtrate is separated
  8. dry with materialthe collected organic layer is dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product is purified by ISCO chromatography
  11. washeluting with ethyl acetate in hexanes from 25% to 100%

Sources & evidence

ORD record
ord-1f2325777c53482194a0e54619fb7cdc
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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