Reaction equation
[CH3:1][C:2]1[C:3](=O)[NH:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][C:7]=1[CH3:8].O(Cl)[Cl:19].[P+5]>CN(C)C=O>[Cl:19][C:3]1[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=[C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:4]=1Participants
Procedure
A solution of 5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one (7.0 g, 32.6 mmol, Step B) in phosphorus (V) oxychloride (30 mL) with addition of 1 drop of dimethylformamide was refluxed overnight under nitrogen. Then excess phosphorus (V) oxychloride was removed under reduced pressure. Toluene (30 mL) was added, and the reaction mixture was evaporated under reduced pressure. The residue was diluted with 5% aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×200 mL). The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography eluted with hexane/ethyl acetate (2:1). The titled compound 6.1 g (74%) was obtained as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.10 (s, 3H), 2.39 (s, 3H), 4.54 (s, 2H), 7.20-7.30 (m, 2H), 7.68-7.76 (m, 2H), 7.76 (bs, 1H).
Workup
- temperaturewas refluxed overnight under nitrogen
- customThen excess phosphorus (V) oxychloride was removed under reduced pressure
- additionToluene (30 mL) was added
- customthe reaction mixture was evaporated under reduced pressure
- additionThe residue was diluted with 5% aqueous sodium bicarbonate (100 mL)
- extractionextracted with ethyl acetate (2×200 mL)
- customThe solvent was evaporated under reduced pressure
- washeluted with hexane/ethyl acetate (2:1)
Sources & evidence
- ORD record
- ord-b29a66f33a4d443984c44429506d74d6
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Linked notes
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