Sodium Hydroxide → 4-Amino-2-(2-pyridylmethylthio)-pyrimidine

HRID 1637711Notes

Reaction equation

HRID 1637711 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([SH:8])[N:3]=1.[OH-].[Na+].[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17]Cl>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23393Picolyl chlorideHCID 178507909HCID 178507909, compound

Product 1

HCID 155501504-Amino-2-(2-pyridylmethylthio)-pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

4-Amino-2-mercaptopyrimidine (0.40 g, 3.15 mmol) is slurried in ethanol (2 ml) and 3.25 M NaOH (2.0 ml, 6.5 mmol) is added. The solution is heated to reflux for 10 minutes and after cooling to 22° C., 2-picolyl chloride*HCl (0.49 g, 2.98 mmol) is added. The solution is heated to reflux for an additional 15 minutes. The solution is cooled and concentrated in vacuo. The residue is dissolved in 1 N HCl and diluted with ethyl acetate. The mixture is neutralized with NaOH to pH 8 and the aqueous layer is separated and washed twice with ethyl acetate. The combined organic layers are washed with saturated NaHCO3, saturated NaCl, dried with MgSO4 and concentrated in uacuo, mp 133-134° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 10 minutes
  3. temperatureThe solution is heated
  4. temperatureto reflux for an additional 15 minutes
  5. temperatureThe solution is cooled
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue is dissolved in 1 N HCl
  8. additiondiluted with ethyl acetate
  9. customthe aqueous layer is separated
  10. washwashed twice with ethyl acetate
  11. washThe combined organic layers are washed with saturated NaHCO3, saturated NaCl
  12. dry with materialdried with MgSO4
  13. concentrationconcentrated in uacuo, mp 133-134° C.

Sources & evidence

ORD record
ord-2a8033a235b249c5a4d31307aecc3660
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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