Реакция #163551

Уравнение реакции

triethylamine

3,5-dimethyl-benzene-1,2-diamine

Na2S2O5

sodium metabisulfite

4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbaldehyde

→

title compound

[5-(4,6-Dimethyl-1H-benzoimidazol-2-yl)-4-methyl-pyrimidin-2-yl]-[3-(1-methyl-piperidin-4-yl)-propyl]-amine

Растворители

DMF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe resultant mixture was then concentrated
2. 2
   Другоеpartitioned between dichloromethane (0.7 L) and 1 N NaOH (1 L)
3. 3
   workup.STIRRINGThe resultant mixture was stirred for 1 hour
4. 4
   Фильтрацияfiltered
5. 5
   Другоеto isolate the voluminous solid which
6. 6
   Другоеhad formed
7. 7
   ДругоеThe solids were dried
8. 8
   Другоеpartitioned between chloroform (700 mL) and saturated aqueous NaHCO3 (700 mL)
9. 9
   ДругоеThe layers were separated
10. 10
    Сушкаthe organic layer was dried over sodium sulfate
11. 11
    Концентрированиеconcentrated to a residue
12. 12
    ДругоеThe residue was recrystallized in hot heptane/ethyl acetate (1.8:1, 840 mL total volume) with initial
13. 13
    Фильтрацияhot filtration (˜1 g of oily residues removed)
14. 14
    Фильтрацияfinal filter cake
15. 15
    Промывкаwashing with heptane/ethyl acetate (3:1, 250 mL total volume)

Методика

To a 2 L Erlenmeyer flask were added 3,5-dimethyl-benzene-1,2-diamine.2HCl (54.85 g, 262.3 mmol) and Na2S2O5 (64.82 g, 341.0 mmol), as well as 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbaldehyde (prepared as in Example 3 above) (72.5 g, 262.3 mmol) in DMF (725 mL). After addition of triethylamine (73.1 mL, 524.6 mmol), the resultant mixture was warmed on a hot plate with stirring to 90° C. and held at this temperature for 2 hours. The resultant mixture was then concentrated to near dryness and partitioned between dichloromethane (0.7 L) and 1 N NaOH (1 L). The resultant mixture was stirred for 1 hour and then filtered to isolate the voluminous solid which had formed. The solids were dried and then partitioned between chloroform (700 mL) and saturated aqueous NaHCO3 (700 mL). The layers were separated, the organic layer was dried over sodium sulfate and concentrated to a residue. The residue was recrystallized in hot heptane/ethyl acetate (1.8:1, 840 mL total volume) with initial hot filtration (˜1 g of oily residues removed) and final filter cake washing with heptane/ethyl acetate (3:1, 250 mL total volume) to yield the title compound as a crystalline solid.

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