Dichloromethane → 4,6-Dichloro-2-methylpyrimidine

HRID 19504

Reaction equation

HRID 19504 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

4

Reactant 3

HCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 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

  1. temperatureUpon cooling
  2. filtrationfiltered
  3. washIt is then washed with water, saturated aqueous sodium bicarbonate and brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f9d73ccab04499d925e69c5dfa51904
Source dataset
uspto-grants-2010_06
Patent number
US07745445B2

Linked notes

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