Benzyl Alcohol → 2,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidine

HRID 426117Notes

Reaction equation

HRID 426117 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].Cl[C:11]1[N:16]=[C:15](Cl)[C:14]([CH2:18][CH3:19])=[C:13]([Cl:20])[N:12]=1>O>[CH2:1]([O:8][C:11]1[N:16]=[C:15]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([CH2:18][CH3:19])=[C:13]([Cl:20])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 2494552,4,6-Trichloro-5-ethylpyrimidineHCID 5360545Sodium2×

Product 1

HCID 596868662,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidineYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of benzyl alcohol (80 ml) in water bath, was added sodium metal (2.17 g, 94.6 mmol) under nitrogen atmosphere. After complete reaction of sodium metal, the mixture was cooled in an ice bath and 2,4,6-Trichloro-5-ethyl-pyrimidine (10.5 g, 49.6 mmol) was added portionwise. After stirring for 30 min in an ice bath, the reaction mixture was stirred at room temperature for overnight. Excess benzyl alcohol was evaporated in vacuo and the residue was dissolved in ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow oil. The crude product was purified by silica gel column chromatography (eluent, ether:hexane (4:96)) to give 14 g (80%) of a white solid; m.p. 53-54° C.; 1H NMR (200 MHz, CDCl3) δ: 1.14 (3H, t, J=7.4 Hz), 2.70 (2H, q, J=7.4 Hz), 5.41 (2H, s), 5.45 (2H, s), 7.34-7.53 (10H, m); m/z (EI): 354 (M+).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringthe reaction mixture was stirred at room temperature for overnight
  3. customExcess benzyl alcohol was evaporated in vacuo
  4. dissolutionthe residue was dissolved in ether
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give a pale yellow oil
  10. customThe crude product was purified by silica gel column chromatography (eluent, ether:hexane (4:96))

Sources & evidence

ORD record
ord-ffa5d377f9d4465b848946edb1cb2975
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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