4-(Dimethoxymethyl)-2-(methylthio)-pyrimidine Chemical Properties

Boiling point:

273.0±25.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

0.37±0.31(Predicted)

Appearance

light yellow liquid

4-(Dimethoxymethyl)-2-(methylthio)-pyrimidine Usage And Synthesis

Synthesis

General procedure: 2-methylthiopyrimidine-4-carbaldehyde dimethyl acetal (19.2 mL, 159.1 mmol) was mixed with N,N-dimethylformamide dimethyl acetal (21.12 mL, 159.1 mmol) in a 500 mL flask and the reaction was heated at 100 °C for 4.5 hours. After the reaction was completed, thiourea (11.0 g, 144.5 mmol), NaOMe (25 wt% MeOH solution, 39.7 mL, 173 mmol) and 30 mL of MeOH were added to the flask, and the reaction continued to be heated at 65°C for 18 hours. At the end of the reaction, the reaction solution was cooled to 25 °C and MeI (10.8 mL, 173 mmol) was added slowly over 5 min (note exothermic). After continuing the reaction for 3 h, the reaction solution was diluted with 250 mL of H2O and extracted with EtOAc (3 × 100 mL). The organic phases were combined, dried over Na2SO4 and concentrated to give 4-(dimethoxymethyl)-2-methylthiopyrimidine (26.8 g, 93% yield) as a brown oil.

References

[1] Patent: US5593991, 1997, A
[2] Patent: US5593992, 1997, A
[3] Patent: US5670527, 1997, A
[4] Patent: US5739143, 1998, A
[5] Patent: US5658903, 1997, A

4-(Dimethoxymethyl)-2-(methylthio)-pyrimidine(180869-36-7)Related Product Information

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