Dimethylacetamide → 4-Bromo-5-ethyl-6-[4-(aminomethyl-2-pyridinyl)-1-piperidinyl]-pyrimidine

HRID 729759Notes

Reaction equation

C([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])(C)C.Br[C:11]1[C:16]([CH2:17][CH3:18])=[C:15]([Br:19])[N:14]=[CH:13][N:12]=1.CC1[CH2:26][CH2:25][N:24](NC2C=CC=CN=2)[CH2:23][CH2:22]1.[C:34](=O)(O)[O-].[Na+].[CH3:39][N:40](C)C(=O)C>C(OCC)(=O)C.O>[Br:19][C:15]1[C:16]([CH2:17][CH3:18])=[C:11]([N:24]2[CH2:25][CH2:26][CH:9]([C:7]3[C:8]([CH2:39][NH2:40])=[CH:34][CH:6]=[CH:5][N:4]=3)[CH2:22][CH2:23]2)[N:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1.8 ml of diisopropylethylamine is added to a mixture of 657 mg (2.47 mmoles) of 4,6-dibromo-5-ethyl-pyrimidine and 450 mg (2.35 mmoles) of 2-(4-methylpiperidinyl)aminopyridine in 55 ml of N,N-dimethylacetamide. This mixture is heated at 110° C. for 4 hours. Then the solvent is eliminated under reduced pressure (0.2 kPa) and the residue is taken up in a mixture of ethyl acetate, water and a saturated solution of sodium bicarbonate. The organic phase is decanted, dried over magnesium sulphate then condensed under reduced pressure (2 kPa). The brown oil obtained is chromatographed on alumina eluting with the following gradient: heptane-ethyl acetate 80-20 to 70-30. 747 mg (Yield=84%) of expected product is obtained in the form of a beige solid.

Workup

customThe organic phase is decanted
dry with materialdried over magnesium sulphate
customcondensed under reduced pressure (2 kPa)
customThe brown oil obtained
customis chromatographed on alumina eluting with the following gradient

Sources & evidence

ORD record: ord-e39ae227dfdd48efa644945602b6f390
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582640B2

Reaction notes

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