Imidazole → HCID 68974419, compound

To a solution of 4-amino-1-hexyl-1H-pyrimidin-2-one (C) (1.00 g, 5.13 mmol) in dry CH2Cl2 (7 ml) was added N,N carbonyl diimidazole (1.31 g, 5.13 mmol) and the solution was stirred at room temperature for 16 h. The solvent was evaporated and the residue redissolved in dry chloroform. Hexane was then added to precipitate the intermediate, which was dried in vacuo and used directly without further purification. To a solution of the resulting imidazole intermediate (1.0 g, 3.47 mmol) in dry THF (20 ml) was added allyl amine (0.40 ml, 5.33 mmol). The solution was stirred at room temperature for 16 h. the solvent was evaporated in vacuo and the residue was redissolved in chloroform and washed with water and brine. The organic phase was combined and dried over MgSO4 and the solvent evaporated under vacuo to afford crude G, which was purified via flash silica gel chromatography (CHCl3/MeOH, 7:1) to give pure compound M (0.262 g, 30% from the amine)

1. customThe solvent was evaporated
2. dissolutionthe residue redissolved in dry chloroform
3. additionHexane was then added
4. customto precipitate the intermediate, which
5. customwas dried in vacuo
6. customused directly without further purification
7. stirringThe solution was stirred at room temperature for 16 h. the solvent
8. customwas evaporated in vacuo
9. dissolutionthe residue was redissolved in chloroform
10. washwashed with water and brine
11. dry with materialdried over MgSO4
12. customthe solvent evaporated under vacuo
13. customto afford crude G, which
14. customwas purified via flash silica gel chromatography (CHCl3/MeOH, 7:1)

ORD record

ord-a094378aa8404a9a969582d1476de534

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076426B2