Chloroform → 4-Chloro-5-(2-chloroethyl)-6-phenylpyrimidine

HRID 717581Notes

Reaction equation

HRID 717581 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9]O)=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1.C(Cl)(Cl)[Cl:18]>O(Cl)Cl.[P]>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][Cl:18])=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 898153532-(4-Chloro-6-phenylpyrimidin-5-yl)ethanol

Product 1

HCID 898145964-Chloro-5-(2-chloroethyl)-6-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 178479709HCID 178479709, compoundSolvent

Procedure

To a stirred solution of 2-(4-chloro-6-phenylpyrimidin-5-yl)ethanol (340 mg) in dry chloroform (10 mL), phosphorus oxy chloride (2 mL) was slowly added under nitrogen atmosphere at 0° C. The reaction mixture was stirred at room temperature for 2 hours and solvents were removed under reduced pressure. The resulting oil was diluted with dichloromethane (50 mL), washed with 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to gave crude 4-chloro-5-(2-chloroethyl)-6-phenylpyrimidine (150 mg) as viscous liquid, which was used as was. 1H NMR (DMSO-d6): δ 2.89-2.94 (t, 2H), 3.54-3.55 (t, 2H), 7.48-7.59 (m, 5H), 8.91 (s, 1H).

Workup

  1. customsolvents were removed under reduced pressure
  2. additionThe resulting oil was diluted with dichloromethane (50 mL)
  3. washwashed with 10% NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e4c784f805b34ebe87977524d9745993
Source dataset
uspto-grants-2015_11
Patent number
US09193725B2

Reaction notes

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