ChemicalBook CAS DataBase List Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI)

Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI) synthesis

6synthesis methods

Product Name:Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI)
CAS Number:67434-65-5
Molecular formula:C6H7ClN2
Molecular Weight:142.59

4316-97-6 Synthesis

4316-97-6
200 suppliers
$8.00/1g

13061-96-6
298 suppliers
$6.00/1g

Pyrimidine, 4-chloro-5,6-dimethyl- (7CI,9CI)

67434-65-5
41 suppliers
$83.00/100mg

Yield:67434-65-5 41%

Reaction Conditions:

with caesium carbonate;tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide;toluene at 140; for 1 h;Irradiation;

Steps:

8

To a mixture of 4,6-dichloro-5-methylpyrimidine (available from Sigma- Aldrich No.595446) (0.50 g, 3.07 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.18 g, 0.15 mmol) in toluene (6 ml) and DMF (1 ml) was added cesium carbonate (3 g, 9.20 mmol), followed by methylboronic acid (0.20 g, 3.37 mmol). The resulting reaction mixture was heated at 140 ⁰C under microwave irradiation (2 cycles x 30 min), allowed to cool down to room temperature and filtered. Solvents were removed under reduced pressure. The residue was taken-up in EtOAc and washed with a saturated NaHCO₃ aqueous solution and brine. The organic phase was separated, dried (Na₂SO₄), filtered and concentrated to afford the title compound D8 (0.18 g, 1.26 mmol, 41% yield). UPLC: rt = 0.53 min, peak observed: 143 (M+1-HC1, 100%) and 445 (M+1-HC1, 33%). C₆H₇ClN₂ requires 142. ¹H NMR (400 MHz, CDCl₃) δ(ppm): 8.70 (s, 1 H), 2.57 (s, 3 H), 2.39 (s, 3 H).

References:

WO2009/3997,2009,A1 Location in patent:Page/Page column 20-21

34916-78-4 Synthesis