Dichloromethane → 4,6-Dichloro-2-methylpyrimidine

Reaction equation

O[C:2]1[CH:7]=C(O)[N:5]=[C:4]([CH3:9])[N:3]=1.P(Cl)(Cl)([Cl:12])=O.Cl[CH2:16][Cl:17]>>[Cl:12][C:2]1[CH:7]=[C:16]([Cl:17])[N:5]=[C:4]([CH3:9])[N:3]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 24813Phosphorus oxychloride

HCID 178418389HCID 178418389, compound

Product 1

HCID 2349974,6-Dichloro-2-methylpyrimidine

Conditions

Temperature: 95 °C

Procedure

4,6-Dihydroxy-2-methylpyrimidine 21 (1.03 g, 8.1 mmol) is suspended in 2.5 mL phosphorus oxychloride (27.3 mmol). The mixture is heated to 95° C. for 18 hours. Upon cooling, the mixture is diluted with dichloromethane (100 mL) and filtered. It is then washed with water, saturated aqueous sodium bicarbonate and brine, then concentrated to yield 4,6-dichloro-2-methylpyrimidine 22 as a white powder. 1H-NMR (400 MHz, CDCl3) δ=7.45 (s, 1H), 2.77 (s, 3H). MS calculated for C5H5Cl2N2 (M+H+) 162.99. found 163.2.

Workup

temperatureUpon cooling
filtrationfiltered
washIt is then washed with water, saturated aqueous sodium bicarbonate and brine
concentrationconcentrated

Sources & evidence

ORD record: ord-9f9d73ccab04499d925e69c5dfa51904
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745445B2

Reaction notes

Loading…